Dichloromethane → HCID 67182634, compound

HRID 1951646Notes

Reaction equation

HRID 1951646 reaction equation
Br[C:2]1[C:6]2[N:7]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)[CH:8]=[CH:9][C:5]=2[S:4][CH:3]=1.C(Cl)Cl.CCN(CC)CC.C[CH2:32][O:33][C:34](C)=[O:35]>CS(C)=O.CO.O>[CH3:32][O:33][C:34]([C:2]1[C:6]2[N:7]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)[CH:8]=[CH:9][C:5]=2[S:4][CH:3]=1)=[O:35]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 582976723-Bromo-4-(4-trifluoromethyl-benzyl)-4H-thieno[3,2-b]pyrrole

Product 1

HCID 67182634HCID 67182634, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

A mixture of 2.0 g of the product of Step 5, 0.54 g of PdCl2dppf.CH2Cl2, and 1.8 ml of Et3N in 60 ml of 2:1 DMSO/MeOH was heated under CO (balloon pressure) at 75° C. for 24 h. The reaction mixture was poured into 400 ml of 1:1 heaxan/EtOAc and stirred with 200 ml of water for 4 h. The organic layer was washed with 100 ml of brine and dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography eluted with a gradient up to 15% EtOAc/hexane to give 1.7 g of the title compound as a light brown solid.

Workup

  1. washThe organic layer was washed with 100 ml of brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluted with a gradient up to 15% EtOAc/hexane

Sources & evidence

ORD record
ord-d118a30cda904dfca9b240e7ad35fcf0
Source dataset
uspto-grants-2013_03
Patent number
US08404736B2

Reaction notes

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