HCID 21202660, compound → HCID 9927613, compound

HRID 1019176Notes

Reaction equation

HRID 1019176 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH:15]=[CH:14][S:13][C:12]2([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)C(O)=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>N1C2C(=CC=CC=2)C=CC=1>[NH2:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:15]=[CH:14][S:13][C:12]=2[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

3

Reactant 1

HCID 21202660HCID 21202660, compound

Product 1

HCID 9927613HCID 9927613, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 7047QuinolineSolvent

Procedure

To a solution of 3-(4-(aminosulfonyl)phenyl)-2-(4-fluorophenyl)thiphene-2-carboxylic acid (0.280 g) in quinoline (4.0 mL) was added Cu bronze (0.300 g). After 0.5 h at 180° C. under nitrogen, the reaction mixture was extracted with EtOAc and HCl 3N, dried over Na2SO4 and purified by flash chromatography (30% EtOAc in hexane) to give the title compound as a white solid (0.180 g). 1H NMR (CD3COCD3): d 6.60 (2H, bs), 7.15 (2H, t), 7.29 (1H, d), 7.35 (2H, q), 7.45 (2H, d), 7.60 (1H, d), 7.83 (2H, d).

Workup

  1. extractionthe reaction mixture was extracted with EtOAc and HCl 3N
  2. dry with materialdried over Na2SO4
  3. custompurified by flash chromatography (30% EtOAc in hexane)

Sources & evidence

ORD record
ord-44e852c0103b4945918e89888140ea1c
Source dataset
uspto-grants-2002_11
Patent number
US06486194B2

Reaction notes

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