Quinolin-6-ylboronic Acid (contains varying amounts of Anhydride) → (+/-)-{9-[(4-chlorophenyl)thio]-6-fluoro-8-quinolin-6-yl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl}acetic acid

HRID 857417Notes

Reaction equation

HRID 857417 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:37]2[C:32](=[CH:33][C:34](B(O)O)=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1>>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([S:20][C:11]2[C:12]3[C:13]([C:34]4[CH:33]=[C:32]5[C:37](=[CH:36][CH:35]=4)[N:28]=[CH:29][CH:30]=[CH:31]5)=[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 4192671Quinolin-6-ylboronic Acid (contains varying amounts of Anhydride)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 58760746(+/-)-{9-[(4-chlorophenyl)thio]-6-fluoro-8-quinolin-6-yl-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 quinolin-6-ylboronic acid, the title compound was synthesized following the procedures described in Example 108.

Sources & evidence

ORD record
ord-63780ffdd7294110b49622f1bacd8973
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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