Water → HCID 57458730, compound

HRID 1673018Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:24])[CH2:4][O:5][C:6]1[CH:10]=[C:9]([C:11]2[S:12][C:13](Br)=[CH:14][CH:15]=2)[N:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[N:7]=1.[CH3:25][S:26]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)(=[O:28])=[O:27].C([O-])([O-])=O.[Na+].[Na+].O>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:8]1[C:9]([C:11]2[S:12][C:13]([C:33]3[CH:32]=[CH:31][CH:30]=[C:29]([S:26]([CH3:25])(=[O:28])=[O:27])[CH:34]=3)=[CH:14][CH:15]=2)=[CH:10][C:6]([O:5][CH2:4][C:3]([O:2][CH3:1])=[O:24])=[N:7]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of [5-(5-bromo-thiophen-2-yl)-1-(2-chloro-phenyl)-1H-pyrazol-3-yloxy]-acetic acid methyl ester (1.43 g, 3.33 mmol) in anhydrous THF (13.0 mL) was added sequentially 3-methylsulfonylphenylboronic acid (0.80 g, 4.0 mmol), Pd(PPh3)4 (192 mg, 0.17 mmol), Na2CO3 (1.06 g, 10.0 mmol) and water (1.0 mL). The reaction mixture was heated to reflux at 70° C. for overnight. The solvent was evaporated and the crude residue was purified by flash column chromatography with 50% ethyl acetate in hexane, resulting the product methyl {1-(2-chloro-phenyl)-5-[5-(3-methanesulfonyl-phenyl)-thiophen-2-yl]-1H-pyrazol-3-yloxy}acetate (0.746 g, 45% yield). 1H-NMR (CDCl3): δ 8.17 (m, 1H), 7.83 (m, 2H), 7.55 (m, 3H), 7.40 (m, 3H), 7.33 (m, 1H), 5.91 (s, 1H), 4.70 (s, 2H), 3.81 (s, 3H), 3.09 (s, 3H). MS (ES): 503 [M+H]+.

Workup

temperatureThe reaction mixture was heated
customThe solvent was evaporated
customthe crude residue was purified by flash column chromatography with 50% ethyl acetate in hexane

Sources & evidence

ORD record: ord-d8cf67479d1143beb792b7d962594947
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998995B2

Reaction notes

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