Potassium Carbonate → HCID 86685325, 화합물

HRID 1853044노트

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HRID 1853044 반응식
Cl[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[N:3]=1.CC1(C)C(C)(C)OB([C:31]2[CH:32]=[N:33][NH:34][CH:35]=2)O1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:33]1[CH:32]=[C:31]([C:2]2[N:7]3[CH:8]=[CH:9][N:10]=[C:6]3[CH:5]=[C:4]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[CH:13][CH:12]=3)[N:3]=2)[CH:35]=[N:34]1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 866853244-(4-(5-Chloroimidazo[1,2-c]pyrimidin-7-yl)phenyl)morpholine

생성물 1

HCID 86685325HCID 86685325, 화합물수율 36.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
100 °C

실험 절차

4-(4-(5-Chloroimidazo[1,2-c]pyrimidin-7-yl)phenyl)morpholine (0.0400 g, 0.127 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.0370 g, 0.191 mmol) and potassium carbonate (0.0527 g, 0.381 mmol) were suspended in a mixture of DME (2 mL) and water (1 mL) and de-gassed with argon for 5 minutes. Tetrakis(triphenylphosphine)palladium (0) (0.00734 g, 0.00635 mmol) was added and the reaction sealed and heated at 100° C. for 2 hours. The reaction mixture was concentrated under reduced pressure. The residue was partitioned between saturated aqueous NaHCO3 and EtOAc. The organics were washed with brine, dried, MgSO4 and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (eluant: 0.5%-6% (9:1 MeOH:NH4OH)/DCM) to furnish 4-(4-(5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-7-yl)phenyl)morpholine (0.0160 g, 0.046 mmol, 36.4% yield). MS (apci) m/z=347.1 (M+H).

후처리

  1. customde-gassed with argon for 5 minutes
  2. customthe reaction sealed
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe residue was partitioned between saturated aqueous NaHCO3 and EtOAc
  5. washThe organics were washed with brine
  6. customdried
  7. concentrationMgSO4 and concentrated under reduced pressure
  8. customto afford the crude material, which
  9. customwas purified by flash column chromatography (eluant: 0.5%-6% (9:1 MeOH:NH4OH)/DCM)

출처 및 근거

ORD 기록
ord-450f629c401d4bfc8d8e6a845f758948
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962596B2

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