Sodium Carbonate → (4-{4-[2-(3-Fluorophenylamino)-pyrimidin-5-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

HRID 76026ノート

反応式

HRID 76026 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)=[N:6][CH:7]=1.[CH3:16][O:17][C:18](=[O:41])[CH2:19][CH:20]1[CH2:25][CH2:24][CH:23]([C:26]2[CH:31]=[CH:30][C:29](B3OC(C)(C)C(C)(C)O3)=[CH:28][CH:27]=2)[CH2:22][CH2:21]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[CH3:16][O:17][C:18](=[O:41])[CH2:19][CH:20]1[CH2:21][CH2:22][CH:23]([C:26]2[CH:27]=[CH:28][C:29]([C:2]3[CH:3]=[N:4][C:5]([NH:8][C:9]4[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=4)=[N:6][CH:7]=3)=[CH:30][CH:31]=2)[CH2:24][CH2:25]1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 57992171Methyl 2-(trans-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclohexyl)acetateHCID 638743875-bromo-N-(3-fluorophenyl)pyrimidin-2-amine

生成物 1

HCID 66615836(4-{4-[2-(3-Fluorophenylamino)-pyrimidin-5-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
125 °C

実験手順

The mixture of (5-bromopyrimidin-2-yl)-(3-fluorophenyl)-amine (75 mg, 0.28 mmol), {4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester (Patent WO2004 047755) (100 mg, 0.28 mmol), PdCl2dppf (12 mg, 0.014 mmol), sodium carbonate (2M solution, 0.35 mL) and DME (2 mL) is heated in a microwave at 125° C. for 15 min. The reaction mixture is extracted with EtOAc, washed with NH4Cl solution. The organic phase is dried with MgSO4, filtered and it is used directly in the next step: (M+H)+420.3.

後処理

  1. extractionThe reaction mixture is extracted with EtOAc
  2. washwashed with NH4Cl solution
  3. dry with materialThe organic phase is dried with MgSO4
  4. filtrationfiltered

出典と根拠

ORDレコード
ord-fb8c687d68c842da8c05ad1306d53884
出典データセット
uspto-grants-2014_09
特許番号
US08835451B2

反応ノート

読み込み中…