Sodium Carbonate → 1-Amino-7-[3-(trifluoromethyl)phenyl][1]benzothieno[3,2-c]pyridine-4-carboxamide

HRID 1896535ノート

反応式

HRID 1896535 の反応式
[NH2:1][C:2]1[C:7]2[C:8]3[CH:14]=[CH:13][C:12](Br)=[CH:11][C:9]=3[S:10][C:6]=2[C:5]([C:16]([NH2:18])=[O:17])=[CH:4][N:3]=1.B(O)(O)[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[NH2:1][C:2]1[C:7]2[C:8]3[CH:14]=[CH:13][C:12]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=4)=[CH:11][C:9]=3[S:10][C:6]=2[C:5]([C:16]([NH2:18])=[O:17])=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 235819291-Amino-7-bromo[1]benzothieno[3,2-c]pyridine-4-carboxamide

生成物 1

HCID 235819951-Amino-7-[3-(trifluoromethyl)phenyl][1]benzothieno[3,2-c]pyridine-4-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

A mixture of 1-amino7-bromo[1]benzothieno[3,2-c]pyridine-4-carboxamide (Example 12, Step 10), 3-trifluoromethylboronic acid (1.5 equiv), PdCl2dppf (0.1 equiv), Na2CO3 1 M (3.0 equiv) in DMF (0.15 M) was heated in the microwave reactor at 120° C. for 10 min. The reaction mixture was partitioned between EtOAc and H2O with the addition of DMSO. The organic phase was separated, dried over Na2SO4, filtered, evaporated and purified by flash chromatography (10% MeOH in CH2Cl2) to provide the title compound.

後処理

  1. customThe reaction mixture was partitioned between EtOAc and H2O with the addition of DMSO
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by flash chromatography (10% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-4c97769a30864db593db72011e5e4043
出典データセット
uspto-grants-2013_08
特許番号
US08518964B2

反応ノート

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