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CAS No. : | 98437-23-1 | MDL No. : | MFCD01075674 |
Formula : | C8H7BO2S | Boiling Point : | - |
Linear Structure Formula : | (C6H4CHCS)B(OH)2 | InChI Key : | YNCYPMUJDDXIRH-UHFFFAOYSA-N |
M.W : | 178.02 | Pubchem ID : | 2359 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90℃; for 15h; | A mixture of 5-bromo-7-iodo-/H-indazole (Preparation No.22a, 30.0 g, 92.9 mmol) and thianapthene-2-boronc acid (21.5 g, 120.7 mmol), DME (480 mL), water (48 mL), Na2CO3 (29.5 g, 279 mmol) and tetrakis triphenylphosphine palladium (0) (8.6 g, 7.43 mmol) was heated at about 90 0C in an oil bath under an atmosphere of nitrogen for about 15 hours. The solvent was removed under reduced pressure and the residue was suspended in a mixture of ethyl acetate (600 mL) and water (300 mL). The mixture was stirred for about 30 minutes and the resulting solid was collected by filtration and dried to yield 7-Benzo[b]ihiophen-2-yl-5-bromo-lH-indazole (21.4 g, 70%); (DMSO-^6, 400 MHz) δ 13.63 (s, IH), 8.24 (s, IH), 8.05-8.09 (m, 3H), 7.92 (d, IH), 7.65 (s, IH), 7.16 (m, 2H); RP-HPLC (Table 1, Method e) Rt = 2.69 min; m/v. (M-H)' 328.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | palladium diacetate; In N,N-dimethyl-formamide; at 60 - 90℃; for 5 - 16h; | Example 44 Preparation of QR-0311[00400] Compound QR-031 1 was prepared by reactions depicted in Scheme 50 below.[00401] The following General Procedure H was used. <n="125"/>General Procedure H[00402] Arylbromide or aryliodide (1 mmol). boric acid ( 1.2 mmol) andPd(OAc)2 (0.05 mmol) in DMF (5 niL) were stirred under argon at 60-90 0C for 5-16 h. The mixture was then cooled to room temperature, ethyl acetate (50 mL) was added and the mixture washed with brine 3 times (50 mL). The organic layer wasdried with MgSO4 and concentrated. The residue was purified by flash columnchromatography.100403] General Procedure H was used to yield 259 (63% yield). 1H NMR(CDCl3): 2.38 (s, 3H). 7.30 (d, 2H. J=8.4). 7.37-7.41 (m, 2H), 7.55 (s, I H), 7.64 (d.1 H. J=8.6), 7.82-8-7.86 (m, 4H), 7.96 (s. 1 H), 8.14 (d. 1 H, .1=8.6). 8.31 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 155℃; for 0.333333h;Microwave irradiation; | General procedure: To a mixture of compound 7a (1 mmol), the corresponding (het)arylboronic acid 10 (1.2 mmol), Pd(PPh3)4 (58 mg, 0.05 mmol) in degassed THF (3 mL), a solution of K2CO3 (346 mg, 2.5 mL) in water (4 mL) were added. The reaction mixture was microwave irradiated at 155 C (250 W) for 20 min, then solvent was removed in vacuo. Products were isolated by column chromatography (elution with ethyl acetate-hexane, 1 : 2). |
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