Cesium carbonate → HCID 67262142, 화합물

HRID 1039899노트

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HRID 1039899 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([NH:19][C:20]3[N:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][N:21]=3)[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])O1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:72]1[S:76][CH:75]=[N:74][CH:73]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[S:76]1[C:72]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([NH:19][C:20]3[N:25]=[C:24]([C:26]([F:29])([F:27])[F:28])[CH:23]=[CH:22][N:21]=3)[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:73][N:74]=[CH:75]1

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 5460595-BromothiazoleHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67433486Methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}benzoate

생성물 1

HCID 67262142HCID 67262142, 화합물수율 72%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

To a flask containing the product of Step 2 (391 mg, 0.92 mmol), dicyclohexyl[2′,4′,6′-tri(propan-2-yl)biphenyl-2-yl]phosphane (44 mg, 0.092 mmol), Pd2(dba)3 (42 mg, 0.046 mmol), cesium carbonate (602 mg, 1.85 mmol) was added a solution of 5-bromothiazole in a degassed mixture of dioxane (8.4 mL) and water (840 μL). The solution was evacuated and then purged with argon 5 times and then heated at 90° C. overnight. The reaction was cooled, diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated. Flash chromatography was used for purification to yield methyl 3-(1,3-thiazol-5-yl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}benzoate (254 mg, 0.67 mmol, 72% yield). MS ESI: [M+H]+ m/z 381.0.

후처리

  1. customThe solution was evacuated
  2. custompurged with argon 5 times
  3. temperatureThe reaction was cooled
  4. additiondiluted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customFlash chromatography was used for purification

출처 및 근거

ORD 기록
ord-84f800b6c73c4fb1810051679e24bec2
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551984B2

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