Potassium Carbonate → (S)-tert-butyl (1-(2-((2-(1H-1,2,3-triazol-1-yl)ethyl)amino)-5-(3-carbamoyl-4-fluorophenyl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

HRID 2170348ノート

反応式

HRID 2170348 の反応式
[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C@@H:15]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:16][C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=3)[C:12](Br)=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1.[C:34]([C:37]1[CH:38]=[C:39](B(O)O)[CH:40]=[CH:41][C:42]=1[F:43])(=[O:36])[NH2:35].C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(C)C=CC=CC=1.CC(O)C.O>[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C@@H:15]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:16][C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=3)[C:12]([C:39]3[CH:40]=[CH:41][C:42]([F:43])=[C:37]([C:34](=[O:36])[NH2:35])[CH:38]=3)=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 44717530(3-Carbamoyl-4-fluorophenyl)boronic acidHCID 90290212(S)-tert-butyl (1-(2-((2-(1H-1,2,3-triazol-1-yl)ethyl)amino)-5-bromopyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

生成物 1

HCID 90290213(S)-tert-butyl (1-(2-((2-(1H-1,2,3-triazol-1-yl)ethyl)amino)-5-(3-carbamoyl-4-fluorophenyl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 66631872toluene IPA water溶媒

反応条件

温度
120 °C

実験手順

In a microwave tube were charged with compound 23C (52 mg, 0.1 mmol), (3-carbamoyl-4-fluorophenyl)boronic acid (27 mg, 0.15 mmol), K2CO3 (41 mg, 0.3 mmol), Pd(dppf)Cl2 (5 mg). To the mixture was added 2 mL of Toluene/2-propanol/H2O (3/1/1). The mixture was heated up to 120° C. for 20 min in a Microwave Synthesizer. The mixture was partitioned between ethyl acetate and water. The organic layer was separated and concentrated to afford crude product used for next step without further purification. MS (m/z) 582.73 [M+H]+.

後処理

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. concentrationconcentrated
  4. customto afford crude product
  5. customused for next step without further purification

出典と根拠

ORDレコード
ord-aeea0dfc57894ec59b56e49d4d221f2f
出典データセット
uspto-grants-2015_06
特許番号
US09050344B2

反応ノート

読み込み中…