Potassium Carbonate → 2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-methanesulfonyl-indol-1-yl)-amide

HRID 2381999노트

반응식

HRID 2381999 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([C:14](Cl)=[O:15])=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:17][S:18]([C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([NH2:30])[CH:25]=[CH:24]2)(=[O:20])=[O:19].C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.O>[CH3:17][S:18]([C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([NH:30][C:14]([C:11]1[CH:10]=[N:9][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:13][CH:12]=1)=[O:15])[CH:25]=[CH:24]2)(=[O:20])=[O:19]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 685555925-Methanesulfonyl-indol-1-ylamineHCID 874965532-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride

생성물 1

HCID 250993522-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-methanesulfonyl-indol-1-yl)-amide수율 34%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매2회

실험 절차

A solution of 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride (0.62 mmol) in EtOAc (10 mL) is added to a stirred solution of 5-methanesulfonyl-indole-1-ylamine (0.62 mmol) and K2CO3 (3.08 mmol) in EtOAc (10 mL) and H2O (10 mL) at 0° C., and the reaction mixture is warmed to rt and stirred overnight. EtOAc is evaporated in vacuo, and the resulting solid is collected by filtration. The solid is triturated with DCM to afford 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-methanesulfonyl-indol-1-yl)-amide (85 mg, 34%) as a solid. MS: 411 (M+H); 1H NMR (300 MHz, CD3OD): δ 3.13 (s, 3H), 6.81 (m, H) 7.25-7.39 (m, H), 7.49-7.67 (m, 3H), 7.72-7.84 (m, H), 8.21-8.32 (m, 2H), 8.39 (d, H), 9.41 (s, 2H).

후처리

  1. customEtOAc is evaporated in vacuo
  2. filtrationthe resulting solid is collected by filtration
  3. customThe solid is triturated with DCM

출처 및 근거

ORD 기록
ord-e2042f2ffaa4442298f6d57d1bcaf63b
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258130B2

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