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

HRID 1773724노트

반응식

HRID 1773724 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 336431-Iodopropane촉매HCID 18180031Water 1,2-dimethoxyethane용매

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온도
120 °C

실험 절차

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.

후처리

  1. concentrationThe reaction was concentrated in vacuo and purification

출처 및 근거

ORD 기록
ord-423093ccbbf04c08895a073aff29a837
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255089B2

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