4-Fluorophenylboronic acid → HCID 59153044, compound

HRID 1966872Notes

Reaction equation

HRID 1966872 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([N:15]([S:17]([C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22](Br)[CH:21]=3)(=[O:19])=[O:18])[CH3:16])[C:9]=2[CH:8]=[N:7]1)C.[F:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1>>[F:32][C:33]1[CH:38]=[CH:37][C:36]([C:22]2[CH:23]=[C:24]([C:26]([F:28])([F:27])[F:29])[CH:25]=[C:20]([S:17]([N:15]([CH3:16])[C@@H:10]3[CH2:11][CH2:12][CH2:13][C:14]4[N:6]([CH2:5][C:4]([OH:3])=[O:31])[N:7]=[CH:8][C:9]3=4)(=[O:18])=[O:19])[CH:21]=2)=[CH:35][CH:34]=1

Participants

3

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 44611514HCID 44611514, compound

Product 1

HCID 59153044HCID 59153044, compoundYield 42%

Procedure

Starting with {(R)-4-[(3-bromo-5-trifluoromethyl-benzenesulfonyl)-methyl-amino]-4,5,6,7-tetrahydro-indazol-1-yl}-acetic acid ethyl ester (prepared by the method analogous to the one described for example 9-1, 1st step) and 4-fluoro-phenylboronic acid, using a method analogous to the one described for example 10-1, {(R)-4-[(4′-fluoro-5-trifluoromethyl-biphenyl-3-sulfonyl)-methyl-amino]-4,5,6,7-tetrahydro-indazol-1-yl}-acetic acid (5 mg, 42%) was obtained. MS cald. for C25H25F4N3O4S 539, obsd. (ESI+) [(M+H)+] 540.

Workup

  1. customprepared by the method analogous to the one

Sources & evidence

ORD record
ord-a9b80e6f673840d7b5f5d476e97ce497
Source dataset
uspto-grants-2013_04
Patent number
US08420675B2

Reaction notes

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