Cesium carbonate → HCID 86713611, 화합물

HRID 2274240

반응식

HRID 2274240 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:12]=[C:13]([NH:17][C:18]([NH:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[O:19])[CH:14]=[CH:15][CH:16]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1.CC1(C)C(C)(C)OB([C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[NH2:36])O1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[NH2:36][C:35]1[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=1[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:12]=[C:13]([NH:17][C:18]([NH:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[O:19])[CH:14]=[CH:15][CH:16]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 27346522-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 574976981-(3-(7-Chloroimidazo[1,2-a]pyridin-3-yl)phenyl)-3-(2,2,2-trifluoroethyl)urea

생성물 1

HCID 86713611HCID 86713611, 화합물수율 90.4%

시약·촉매·용매 2

HCID 178418851HCID 178418851, 화합물촉매HCID 21881883Oxolane--water (1/1)용매

반응 조건

온도
125 °C

실험 절차

To a mixture of 1-(3-(7-chloroimidazo[1,2-a]pyridin-3-yl)phenyl)-3-(2,2,2-trifluoroethyl)urea (20 mg, 0.052 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (15 mg, 0.066 mmol) and cesium carbonate (51 mg, 0.156 mmol) in THF/H2O mixture (2/1, 0.75 ml) was added Pd(PtBu3)2 (3 mg, 0.005 mmol). The vial was degassed for 5 minutes then capped and heated to 125° C. for 20 minutes in a microwave. After cooling to ambient temperature, the reaction mixture was filtered through a celite pad and purified via flash cromatography (0-10% MeOH/DCM gradient containing 10% NH4OH) to yield the title compound (20 mg, 90% yield). MS (ES+) C22H18F3N5O requires: 425. Found: 426 [M+H]+.

후처리

  1. customThe vial was degassed for 5 minutes
  2. customthen capped
  3. temperatureAfter cooling to ambient temperature
  4. filtrationthe reaction mixture was filtered through a celite pad
  5. custompurified via flash cromatography (0-10% MeOH/DCM gradient containing 10% NH4OH)

출처 및 근거

ORD 기록
ord-12e13cabbc014eeca5d111899c7def01
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126951B2

연결된 노트

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