Butyl vinyl ether → HCID 118199865、化合物

HRID 633768ノート

反応式

HRID 633768 の反応式
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]

参加物

8

反応物 4

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

生成物 1

HCID 118199865HCID 118199865、化合物収率 10.1%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 21962138N,N-Dimethylformamide--water (1/1)溶媒

実験手順

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:

後処理

  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)

出典と根拠

ORDレコード
ord-1fa6d819e69744f3a8139099ae0a2087
出典データセット
uspto-grants-2016_04
特許番号
US09321790B2

反応ノート

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