2-Bromo-4-fluorobenzene-1-sulfonyl chloride → Methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-1,2-dihydro-furo[2,3-c]quinoline-6-carboxylate

HRID 927914Notes

Reaction equation

HRID 927914 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]2[C:16]([C@H:17]3[CH2:29][CH2:28][O:27][C@H:18]3[CH2:19]O2)=[CH:15][CH:14]=1)(=[O:11])=[O:10].[NH2:30]C1C(C(OC)=O)=C2C(C3CCOC=3C=N2)=CC=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:12][C:13]1[C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]2[C:16]([C:17]3[CH2:29][CH2:28][O:27][C:18]=3[CH:19]=[N:30]2)=[CH:15][CH:14]=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 86713283Methyl 7-amino-1,2-dihydrofuro[2,3-c]quinoline-6-carboxylate2×

Product 1

HCID 71006928Methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-1,2-dihydro-furo[2,3-c]quinoline-6-carboxylate

Procedure

Prepared by proceeding in a similar manner to Intermediate 18, starting from methyl 7-amino-1,2-dihydrofuro[2,3-c]quinoline-6-carboxylate (Intermediate 23) and 2-bromo-4-fluorobenzenesulfonyl chloride and stirring at room temperature for 3 days.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0b6aa9e0b63d4942a59ece033a458622
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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