Stannane, tributyl-3-thienyl- → (+)-{9-[(4-chlorophenyl)thio]-6-fluoro-8-thien-3-yl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl}acetic acid

HRID 857388Notes

Reaction equation

HRID 857388 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].C([Sn](CCCC)(CCCC)[C:33]1[CH:37]=[CH:36][S:35][CH:34]=1)CCC>>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([S:20][C:11]2[C:12]3[C:13]([C:33]4[CH:37]=[CH:36][S:35][CH:34]=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:22][CH:23]=1

Participants

3

Reactant 2

HCID 10959689Stannane, tributyl-3-thienyl-HCID 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 10182896(+)-{9-[(4-chlorophenyl)thio]-6-fluoro-8-thien-3-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 and tributyl(thien-3-yl)stannane, the title compound was synthesized following the procedures described in Example 42 and Step 10 of Example 7.

Sources & evidence

ORD record
ord-05b1a482d3f648619b3a338a76af0cf1
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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