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

HRID 74548

반응식

HRID 74548 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e7715b4c41a841ddbe40092327e7cbb0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829006B2

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