2-Methyl-5-(trimethylstannyl)thiazole → HCID 86685318, 화합물

HRID 1853027노트

반응식

HRID 1853027 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:12]=2)[N:5]2[CH:21]=[CH:22][N:23]=[C:4]2[CH:3]=1.[CH3:24][C:25]1[S:26][C:27]([Sn](C)(C)C)=[CH:28][N:29]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>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]>[CH3:24][C:25]1[S:26][C:27]([C:2]2[N:7]=[C:6]([C:8]3[CH:9]=[N:10][N:11]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:12]=3)[N:5]3[CH:21]=[CH:22][N:23]=[C:4]3[CH:3]=2)=[CH:28][N:29]=1

참가 물질

5

반응물 3

HCID 102646602-Methyl-5-(trimethylstannyl)thiazoleHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 866852957-chloro-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine

생성물 1

HCID 86685318HCID 86685318, 화합물수율 83.1%

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

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온도
100 °C

실험 절차

A flask charged with 7-chloro-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (Preparation G; 0.200 g, 0.572 mmol) and 2-methyl-5-(trimethylstannyl)thiazole (0.165 g, 0.629 mmol) was evacuated and backfilled with argon before 4 mL of dioxane were added and argon was bubbled through for 5 minutes. Tris(dibenzylideneacetone)dipalladium (0.0523 g, 0.0572 mmol) and dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.0545 g, 0.114 mmol) were added, argon was bubbled through the reaction for 10 minutes. The reaction flask was sealed and heated to 100° C. with stirring for 2 hours. The reaction mixture was loaded directly onto a silica gel column pre-wetted and eluted with a gradient of 25-100% ethyl acetate with 1% ammonium hydroxide to afford 2-methyl-5-(5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-7-yl)thiazole (0.196 g, 0.475 mmol, 83.1% yield). MS (apci) m/z=413.1 (M+H).

후처리

  1. customwas evacuated
  2. additionwere added
  3. customargon was bubbled through for 5 minutes
  4. customargon was bubbled through the reaction for 10 minutes
  5. customThe reaction flask was sealed
  6. washeluted with a gradient of 25-100% ethyl acetate with 1% ammonium hydroxide

출처 및 근거

ORD 기록
ord-f18d837a820e4956ade6d24d15a526b2
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962596B2

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