Dichloromethane → 2-Oxo-1-(4-trifluoromethyl-benzyl)-2,3-dihydro-1H-indole-7-carboxylic acid

HRID 1951652ノート

反応式

HRID 1951652 の反応式
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)[C:8](=[O:22])[CH2:7]2.C(Cl)Cl.CCN(CC)CC.CC[O:35][C:36](C)=[O:37]>CS(C)=O.CO.O>[O:22]=[C:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:36]([OH:37])=[O:35])[CH:3]=[CH:4][CH:5]=2)[N:9]1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 582976787-Bromo-1-(4-trifluoromethylbenzyl)-1,3-dihydro-indol-2-one

生成物 1

HCID 582977002-Oxo-1-(4-trifluoromethyl-benzyl)-2,3-dihydro-1H-indole-7-carboxylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 22036561Dimethyl sulfoxide methanol溶媒

実験手順

A mixture 2.8 g of 7-bromo-1-(4-trifluoromethylbenzyl)-1,3-dihydro-indol-2-one, 0.70 g of PdCl2dppf.CH2Cl2, and 2.34 ml of Et3N in 75 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 150 ml of brine and dried over Na2SO4, filtered through a pad of silica gel, and concentrated. The residue was dissolved in 60 ml THF, 20 ml of MeOH and 20 ml of water, followed by 30 ml of 1N aqueous LiOH solution. After stirring for 5 h at room temperature, 5 ml of AcOH was added and the mixture was extracted with 250 ml of EtOAc. The organic layer was washed with 50 ml of brine and dried over Na2SO4, filtered, and concentrated. The residue was swished from 50 ml of 1:1 hexane/EtOAc to give 1.2 g of the title compound as a light brown solid.

後処理

  1. washThe organic layer was washed with 150 ml of brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered through a pad of silica gel
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 60 ml THF
  6. addition5 ml of AcOH was added
  7. extractionthe mixture was extracted with 250 ml of EtOAc
  8. washThe organic layer was washed with 50 ml of brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-b9dfcc9a1b9e474f8e4465e9589406b0
出典データセット
uspto-grants-2013_03
特許番号
US08404736B2

反応ノート

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