2-Bromo-4-fluorobenzene-1-sulfonyl chloride → Methyl (1aRS,7bSR)-5-(2-bromo-4-fluorobenzenesulfonylamino)-1,1-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

HRID 927947Notes

Reaction equation

HRID 927947 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9](NC1C(C(OC)=O)=C2C([C@H]3CCO[C@H]3CO2)=CC=1)(=[O:11])=[O:10].[NH2:30][C:31]1[C:40]([C:41]([O:43][CH3:44])=[O:42])=[C:39]2[C:34]([CH:35]3[C:45]([F:47])([F:46])[CH:36]3[CH2:37][O:38]2)=[CH:33][CH:32]=1.BrC1C=C(F)C=CC=1S(Cl)(=O)=O>>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:30][C:31]1[C:40]([C:41]([O:43][CH3:44])=[O:42])=[C:39]2[C:34]([CH:35]3[C:45]([F:47])([F:46])[CH:36]3[CH2:37][O:38]2)=[CH:33][CH:32]=1)(=[O:11])=[O:10]

Participants

4

Reactant 3

HCID 27782162-Bromo-4-fluorobenzene-1-sulfonyl chlorideHCID 86713280methyl cis-(3aRS,9bRS)-7-(2-bromo-4-fluorobenzenesulfonylamino)-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylateHCID 86713303Methyl (1aRS,7bSR)-5-amino-1,1-difluoro-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate2×

Product 1

HCID 86713302Methyl (1aRS,7bSR)-5-(2-bromo-4-fluorobenzenesulfonylamino)-1,1-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

Procedure

Prepared by proceeding in a similar manner to Intermediate 18, starting from methyl (1aRS,7bSR)-5-amino-1,1-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 61) and 2-bromo-4-fluorobenzene sulfonyl chloride, as a colourless foam.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-c261dd53226142c3a27b41b0d03e7780
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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