1-Methyl-5-(tributylstannyl)-1H-pyrazole → (+/-)-[9-[(4-chlorophenyl)thio]-6-fluoro-8-(1-methyl-1H-pyrazol-5-yl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl]acetic acid

HRID 857382Notes

Reaction equation

HRID 857382 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].[CH3:28][N:29]1[C:33]([Sn](CCCC)(CCCC)CCCC)=[CH:32][CH:31]=[N:30]1>>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([S:20][C:11]2[C:12]3[C:13]([C:33]4[N:29]([CH3:28])[N:30]=[CH:31][CH:32]=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 218674551-Methyl-5-(tributylstannyl)-1H-pyrazoleHCID 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 10226217(+/-)-[9-[(4-chlorophenyl)thio]-6-fluoro-8-(1-methyl-1H-pyrazol-5-yl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl]acetic acid

Procedure

Starting from (+/−)-methyl{8-bromo-9-[(4-chlorophenyl)thio]-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl}acetate (Example 7, Step 9, 200 mg, 0.43 mmol) and 1-methyl-5-(tributylstannyl)-1H-pyrazole (239 mg, 0.64 mmol), the title compound was synthesized following the procedures described in Example 42 and Step 10 of Example 7.

Sources & evidence

ORD record
ord-5aae595fad5a468081cac0ceb214d53c
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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