Potassium Carbonate → 2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid pyrrolo[3,2-b]pyridin-1-ylamide

HRID 2382009

反応式

HRID 2382009 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([CH3:14])[C:11]([C:15](Cl)=[O:16])=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[N:18]1([NH2:27])[C:26]2[C:21](=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19]1.C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O.O>[N:18]1([NH:27][C:15]([C:11]2[C:12]([CH3:14])=[N:13][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:9][CH:10]=2)=[O:16])[C:26]2[C:21](=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19]1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 19601545Pyrrolo[3,2-b]pyridin-1-ylamineHCID 874957952-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid chloride

生成物 1

HCID 250998322-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid pyrrolo[3,2-b]pyridin-1-ylamide収率 24.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

A solution of 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid chloride (0.45 mmol) in EtOAc (8 mL) is added to a stirred solution of pyrrolo[3,2-b]pyridin-1-ylamine (0.45 mmol) and potassium carbonate (0.45 mmol) in EtOAc (4 mL) and H2O (8 mL) at rt and the reaction mixture is stirred at rt overnight. EtOAc is evaporated in vacuo, and the resulting solid is collected by filtration. The solid is purified by silica gel chromatography eluting with 20-80% EtOAc in heptane to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid pyrrolo[3,2-b]pyridin-1-ylamide (38 mg, 24%) as a solid. MS: 348 (M+H); 1H NMR (300 MHz, CDCl3): δ 2.76 (s, 3H), 6.59 (m, H) 7.07-7.64 (m, 4H), 7.96 (m, H), 8.23 (m, H), 8.32 (m, 2H), 9.12 (s, H), 10.01 (br, N—H).

後処理

  1. customEtOAc is evaporated in vacuo
  2. filtrationthe resulting solid is collected by filtration
  3. customThe solid is purified by silica gel chromatography
  4. washeluting with 20-80% EtOAc in heptane

出典と根拠

ORDレコード
ord-affce6f8a045483287bb1cbcbf6cdce8
出典データセット
uspto-grants-2012_09
特許番号
US08258130B2

関連ノート

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