(3-(1H-pyrazol-1-yl)phenyl)boronic acid → (+/-)-{9-[(4-CHLOROPHENYL)THIO]-6-FLUORO-8-[3-(1H-PYRAZOL-1-YL)PHENYL]-2,3-DIHYDRO-1H-PYRROLO[1,2-a]INDOL-1-YL}ACETIC ACID

HRID 857414Notes

Reaction equation

HRID 857414 reaction equation
C[CH:2]([CH:6]1[C:10]2=[C:11]([S:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[C:12]3[C:13](Br)=[CH:14][C:15]([F:18])=[CH:16][C:17]=3[N:9]2[CH2:8][CH2:7]1)[C:3]([O-:5])=[O:4].[N:28]1([C:33]2[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=2)[CH:32]=[CH:31][CH:30]=[N:29]1>>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([S:20][C:11]2[C:12]3[C:13]([C:37]4[CH:36]=[CH:35][CH:34]=[C:33]([N:28]5[CH:32]=[CH:31][CH:30]=[N:29]5)[CH:38]=4)=[CH:14][C:15]([F:18])=[CH:16][C:17]=3[N:9]3[CH2:8][CH2:7][CH:6]([CH2:2][C:3]([OH:5])=[O:4])[C:10]=23)=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 16640530(3-(1H-pyrazol-1-yl)phenyl)boronic acidHCID 21867555(+)-methyl{8-bromo-9-[(4-chlorophenyl)thio]-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl}acetate

Product 1

HCID 58760773(+/-)-{9-[(4-CHLOROPHENYL)THIO]-6-FLUORO-8-[3-(1H-PYRAZOL-1-YL)PHENYL]-2,3-DIHYDRO-1H-PYRROLO[1,2-a]INDOL-1-YL}ACETIC ACID

Procedure

Starting from (+/−)-methyl[8-bromo-9-[(4-chlorophenyl)sulfanyl]-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl]acetate (Example 7, Step 9) and 3-(1H-pyrazol-1-yl)phenylboronic acid, the title compound was synthesized following the procedures described Example 108.

Sources & evidence

ORD record
ord-f7ee471095614e03b7fa6dbc3aac220d
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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