Diethyl Ether → HCID 67970696、化合物

HRID 241436ノート

反応式

HRID 241436 の反応式
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]

参加物

9

反応物 5

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 67970619HCID 67970619、化合物HCID 178418416HCID 178418416、化合物

生成物 1

HCID 67970696HCID 67970696、化合物収率 77%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5f5bb4786d9242949fde6abeaade1c95
出典データセット
uspto-grants-2014_02
特許番号
US08648200B2

反応ノート

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