Diethyl Ether → HCID 67970696, 화합물

HRID 241436노트

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HRID 241436 반응식
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]([F:12])[F:11])[C:5]#[N:6].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C]=[O:50].C[CH2:52][O:53][CH2:54]C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C.CO>[C:5]([C:4]1[CH:7]=[CH:8][C:9]([CH:10]([F:12])[F:11])=[C:2]([CH:3]=1)[C:52]([O:53][CH3:54])=[O:50])#[N:6]

참가 물질

9

반응물 5

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 67970619HCID 67970619, 화합물HCID 178418416HCID 178418416, 화합물

생성물 1

HCID 67970696HCID 67970696, 화합물수율 77%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

Purge a mixture of 3-bromo-4-(difluoromethyl)benzonitrile (8.87 g, 38.2 mmol, 1.0 equiv), triethylamine (16.0 mL, 114.7 mmol, 3.0 equiv), MeOH (70 mL), and DMF (120 mL) with nitrogen; then treat the mixture with palladium(II) acetate (867 mg, 3.82 mmol, 0.1 equiv) and 1,3-bis(diphenylphosphino)propane (1.61 g, 3.82 mmol, 0.1 equiv). Stir the mixture under 138 kPag of carbon monoxide at room temperature for two days and then 80° C. for one day. Cool the mixture to room temperature, and dilute with Et2O (300 mL). Wash the mixture with water and saturated sodium chloride, and separate the organic layer. Dry the organic layer over sodium sulfate; filter; collect the filtrate; and concentrate under reduced pressure. Subject the resulting crude material to silica gel chromatography eluting with a gradient of 10-15% THF/hexanes gradient to give the title compound (6.19 g, 77% yield). ES/MS (m/z) 211 (M).

후처리

  1. customPurge
  2. washWash the mixture with water and saturated sodium chloride
  3. customseparate the organic layer
  4. dry with materialDry the organic layer over sodium sulfate
  5. filtrationfilter
  6. customcollect the filtrate
  7. concentrationand concentrate under reduced pressure
  8. washeluting with a gradient of 10-15% THF/hexanes gradient

출처 및 근거

ORD 기록
ord-5f5bb4786d9242949fde6abeaade1c95
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648200B2

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