Butyl vinyl ether → HCID 118199865, 화합물

HRID 633768노트

반응식

HRID 633768 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]([F:11])[F:10])=[N:6][CH:7]=1.[CH3:12][CH2:13][CH2:14][CH2:15][O:16][CH:17]=[CH2:18].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O.CN(C=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:15]([O:16][C:17]([C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]([F:11])[F:10])=[N:6][CH:7]=1)=[CH2:18])[CH2:14][CH2:13][CH3:12]

참가 물질

8

반응물 4

HCID 8108Butyl vinyl etherHCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 498534165-Bromo-2-(difluoromethoxy)pyridine

생성물 1

HCID 118199865HCID 118199865, 화합물수율 10.1%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 21962138N,N-Dimethylformamide--water (1/1)용매

실험 절차

1 g (4.46 mmol) of 5-bromo-2-difluoromethoxypyridine in 20 mL of H2O/DMF (1/4: v/v), 1.46 mL (11.16 mmol) of N-butyl vinyl ether, 30.68 mg (0.13 mmol) of palladium(II) acetate, 125 mg (0.29 mmol) of 1,3-bis(diphenylphosphino)propane and 746 mg (5.36 mmol) of potassium carbonate are placed in a microwave tube. After microwave irradiation for 1 hour at 120° C., the crude product is taken up in water and extracted with DCM. The organic phase is dried over magnesium sulfate and then evaporated to dryness. The crude product is purified by chromatography on silica gel (eluent: 0/100 EtOAc/heptane to 20/80 EtOAc/heptane over 35 minutes) to give 110 mg of 5-(1-butoxyvinyl)-2-difluoromethoxypyridine, corresponding to the following characteristics:

후처리

  1. customAfter microwave irradiation for 1 hour at 120° C.
  2. extractionextracted with DCM
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe crude product is purified by chromatography on silica gel (eluent: 0/100 EtOAc/heptane to 20/80 EtOAc/heptane over 35 minutes)

출처 및 근거

ORD 기록
ord-1fa6d819e69744f3a8139099ae0a2087
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321790B2

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