methyl 7-(2-bromo-4-fluorobenzenesulfonylamino]-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indole-8-carboxylate → methyl 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indole-8-carboxylate

HRID 715963Notes

Reaction equation

HRID 715963 reaction equation
[CH2:1]([N:3]([CH2:35][CH3:36])[CH2:4]/[CH:5]=[CH:6]\[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([NH:17][C:18]1[C:30]([C:31]([O:33][CH3:34])=[O:32])=[C:22]2O[CH2:24][C@H:25]3[CH2:29][CH2:28][CH2:27][N:26]3[C:21]2=[CH:20][CH:19]=1)(=[O:16])=[O:15])[CH3:2].BrC1C=C(F)C=CC=1S(NC1C=CC2N3CCCC3CC=2C=1C(OC)=O)(=O)=O.C(N(CC)C/C=C\[Sn](CCCC)(CCCC)CCCC)C>>[CH2:1]([N:3]([CH2:35][CH3:36])[CH2:4]/[CH:5]=[CH:6]\[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([NH:17][C:18]1[CH:19]=[CH:20][C:21]2[N:26]3[CH2:27][CH2:28][CH2:29][CH:25]3[CH2:24][C:22]=2[C:30]=1[C:31]([O:33][CH3:34])=[O:32])(=[O:16])=[O:15])[CH3:2]

Participants

4

Reactant 3

HCID 70984706methyl 7-(2-bromo-4-fluorobenzenesulfonylamino]-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indole-8-carboxylate2×HCID 86684726N,N-diethyl-N-((Z)-1-tributylstannanylprop-1-en-3-yl)amine2×HCID 86712100methyl (R)-7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzene-sulfonylamino]-2,3,3a,4-tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-6-carboxylate

Product 1

HCID 86712102methyl 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indole-8-carboxylate

Procedure

Prepared by proceeding in a similar manner to Intermediate 1, starting from methyl 7-(2-bromo-4-fluorobenzenesulfonylamino]-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indole-8-carboxylate (Intermediate 28) and N,N-diethyl-N—((Z)-1-tributyl-stannanylprop-1-en-3-yl)-amine (Intermediate 3).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-18e14da7432f445fbc74693bee7d4dd1
Source dataset
uspto-grants-2015_11
Patent number
US09187494B2

Reaction notes

Loading…