acetic acid (S)-1-((Z)-3-tributylstannanylallyl)-pyrrolidin-3-yl ester → Methyl 7-{4-fluoro-2-[(Z)-3-((S)-3-acetoxypyrrolidin-1-yl)-prop-1-enyl]-benzenesulfonylamino}-4H-furo[2,3-c]chromene-6-carboxylate

HRID 1778398Notes

Reaction equation

HRID 1778398 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20]3[C:15]([C:16]4[CH:28]=[CH:27][O:26][C:17]=4[CH2:18][O:19]3)=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[C:4](/[CH:29]=[CH:30]\[CH2:31][N:32]2[CH2:36][CH2:35][C@@H:34]([O:37][C:38](=[O:40])[CH3:39])[CH2:33]2)[CH:3]=1.BrC1C=C(F)C=CC=1S(NC1C(C(OC)=O)=C2C(C3C=COC=3CO2)=CC=1)(=O)=O.C([Sn](CCCC)(CCCC)/C=C\CN1CC[C@H](OC(=O)C)C1)CCC>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20]3[C:15]([C:16]4[CH:28]=[CH:27][O:26][C:17]=4[CH2:18][O:19]3)=[CH:14][CH:13]=2)(=[O:9])=[O:10])=[C:4](/[CH:29]=[CH:30]\[CH2:31][N:32]2[CH2:36][CH2:35][C@H:34]([O:37][C:38](=[O:40])[CH3:39])[CH2:33]2)[CH:3]=1

Participants

4

Reactant 3

HCID 66685087acetic acid (S)-1-((Z)-3-tributylstannanylallyl)-pyrrolidin-3-yl ester2×HCID 66685486methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-4H-furo[2,3-c]chromene-6-carboxylate2×HCID 68093265methyl 7-{4-fluoro-2-[(Z)-3-((R)-3-acetoxypyrrolidin-1-yl)-prop-1-enyl]-benzenesulfonylamino}-4H-furo[2,3-c]chromene-6-carboxylate

Product 1

HCID 66685731Methyl 7-{4-fluoro-2-[(Z)-3-((S)-3-acetoxypyrrolidin-1-yl)-prop-1-enyl]-benzenesulfonylamino}-4H-furo[2,3-c]chromene-6-carboxylate

Procedure

Prepared by proceeding in a similar manner to Intermediate 82, starting from methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-4H-furo[2,3-c]chromene-6-carboxylate (Intermediate 7) and acetic acid (S)-1-((Z)-3-tributylstannanylallyl)-pyrrolidin-3-yl ester (Intermediate 85).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-a70470aac3d04882bf023e17162763e3
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

Loading…