4-Chloropyridine-2-carboxylic acid → (4-Chloro-pyridin-2-yl)-(4,5-difluoro-2,3-dihydro-indol-1-yl)-methanone

HRID 74548

反応式

HRID 74548 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[F:34][C:35]1[C:43]([F:44])=[CH:42][CH:41]=[C:40]2[C:36]=1[CH2:37][CH2:38][NH:39]2>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([N:39]2[C:40]3[C:36](=[C:35]([F:34])[C:43]([F:44])=[CH:42][CH:41]=3)[CH2:37][CH2:38]2)=[O:10])[CH:3]=1

参加物

5

反応物 3

HCID 2308904-Chloropyridine-2-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 447549184,5-Difluoroindoline hydrochloride

生成物 1

HCID 58386701(4-Chloro-pyridin-2-yl)-(4,5-difluoro-2,3-dihydro-indol-1-yl)-methanone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

0.50 g (3.2 mmol) 4-chloropicolinic acid, 1.1 g (3.4 mmol) TBTU and 0.91 mL (6.5 mmol) TEA were placed in 10 mL DMF. 0.63 g (3.3 mmol) 4,5-difluoroindoline hydrochloride were added. The reaction mixture was stirred overnight at RT and then extracted successively with a 15% potassium carbonate solution, water, a 1M HCl solution and EtOAc. The organic phase was dried, filtered and concentrated to dryness by rotary evaporation. The residue was stirred with diisopropylether and the undissolved solid was suction filtered and dried.

後処理

  1. extractionextracted successively with a 15% potassium carbonate solution, water
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. concentrationconcentrated to dryness by rotary evaporation
  5. stirringThe residue was stirred with diisopropylether
  6. filtrationfiltered
  7. customdried

出典と根拠

ORDレコード
ord-e7715b4c41a841ddbe40092327e7cbb0
出典データセット
uspto-grants-2014_09
特許番号
US08829006B2

関連ノート

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