Potassium Carbonate → 3-(5-Bromo-thiazolo[5,4-b]pyridin-2-ylmethoxy)-2,6-difluoro-benzamide

HRID 538576노트

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HRID 538576 반응식
[Br:1][C:2]1[N:7]=[C:6]2[S:8][C:9]([CH2:11]Br)=[N:10][C:5]2=[CH:4][CH:3]=1.[F:13][C:14]1[C:22]([OH:23])=[CH:21][CH:20]=[C:19]([F:24])[C:15]=1[C:16]([NH2:18])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]2[S:8][C:9]([CH2:11][O:23][C:22]3[C:14]([F:13])=[C:15]([C:19]([F:24])=[CH:20][CH:21]=3)[C:16]([NH2:18])=[O:17])=[N:10][C:5]2=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 451201362,6-Difluoro-3-hydroxybenzamideHCID 866432755-Bromo-2-bromomethyl-thiazolo[5,4-b]pyridine

생성물 1

HCID 866432773-(5-Bromo-thiazolo[5,4-b]pyridin-2-ylmethoxy)-2,6-difluoro-benzamide수율 77%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
25 °C

실험 절차

To a solution of 5-bromo-2-bromomethyl-thiazolo[5,4-b]pyridine (2.0 g, 6.493 mmol) in 10 ml of anhydrous DMF was added 2,6-Difluoro-3-hydroxy-benzamide (1.01 g, 5.84 mmol) and potassium carbonate (3.09 g, 22.72 mmol). The reaction mixture was stirred at 25° C. for 24 h under nitrogen atmosphere. The reaction mixture was evaporated to dryness under reduced pressure and the residue was purified by column chromatography on silica (60-120 M) using ethyl acetate/hexane (50:50) as the eluent to provide the title compound (1.80 g, 69%). 1H NMR (DMSO-d6, 400 MHz): δ 5.72 (s, 2H), 7.12 (t, J=7.60 Hz, 1H), 7.39 (m, 1H), 7.90 (br s, 1H), 8.18 (br s, 1H) and 8.80 (m, 2H). MS ES+ (402.08), HPLC (method I) Rt=15.50 min.

후처리

  1. customThe reaction mixture was evaporated to dryness under reduced pressure
  2. customthe residue was purified by column chromatography on silica (60-120 M)

출처 및 근거

ORD 기록
ord-80a12bcb8058408ab5d31a692dd37015
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865736B2

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