Cesium carbonate → 5-(3,5-dimethylisoxazol-4-yl)-1-methyl-7-(6-(trifluoromethoxy)quinolin-5-yl)-1H-benzo[d]imidazol-2(3H)-one

HRID 1773724ノート

反応式

HRID 1773724 の反応式
[CH3:1][C:2]1[C:6]([C:7]2[CH:17]=[C:16](B3OC(C)(C)C(C)(C)O3)[C:10]3[N:11]([CH3:15])[C:12](=[O:14])[NH:13][C:9]=3[CH:8]=2)=[C:5]([CH3:27])[O:4][N:3]=1.Br[C:29]1[C:38]([O:39][C:40]([F:43])([F:42])[F:41])=[CH:37][CH:36]=[C:35]2[C:30]=1[CH:31]=[CH:32][CH:33]=[N:34]2.C([O-])([O-])=O.[Cs+].[Cs+]>ICCC.COCCOC.O>[CH3:1][C:2]1[C:6]([C:7]2[CH:17]=[C:16]([C:29]3[C:38]([O:39][C:40]([F:41])([F:42])[F:43])=[CH:37][CH:36]=[C:35]4[C:30]=3[CH:31]=[CH:32][CH:33]=[N:34]4)[C:10]3[N:11]([CH3:15])[C:12](=[O:14])[NH:13][C:9]=3[CH:8]=2)=[C:5]([CH3:27])[O:4][N:3]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 1176019505-Bromo-6-(trifluoromethoxy)quinolineHCID 1233347005-(3,5-dimethylisoxazol-4-yl)-1-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one

生成物 1

HCID 1176016625-(3,5-dimethylisoxazol-4-yl)-1-methyl-7-(6-(trifluoromethoxy)quinolin-5-yl)-1H-benzo[d]imidazol-2(3H)-one

試薬・触媒・溶媒 2

HCID 336431-Iodopropane触媒HCID 18180031Water 1,2-dimethoxyethane溶媒

反応条件

温度
120 °C

実験手順

To a microwave vial containing 5-(3,5-dimethylisoxazol-4-yl)-1-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one (52 mg, 0.14 mmol, 1 equiv.) was added 5-bromo-6-(trifluoromethoxy)quinoline (124 mg, 0.42 mmol, 3 equiv.), Cs2CO3 (230 mg, 0.70 mmol, 5 equiv.) and PEPPSI™-IPr catalyst (9.5 mg, 0.014 mmol, 0.1 equiv.) and dissolved in DME-H2O (4 mL, 0.2 M, 2/1, v/v). The mixture was heated to 120° C. for 30 min in microwave. The reaction was concentrated in vacuo and purification was then carried out by reverse phase HPLC.

後処理

  1. concentrationThe reaction was concentrated in vacuo and purification

出典と根拠

ORDレコード
ord-423093ccbbf04c08895a073aff29a837
出典データセット
uspto-grants-2016_02
特許番号
US09255089B2

反応ノート

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