Dimethylformamide → Tert-butyl 9-cyano-2,3-dihydrobenzo[F][1,4]oxazepine-4(5H)-carboxylate

HRID 1514226노트

반응식

HRID 1514226 반응식
FC(F)(F)S(O[C:7]1[C:17]2[O:16][CH2:15][CH2:14][N:13]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)(=O)=O.[CH3:27][N:28](C=O)C>CCOC(C)=O.O.[C-]#N.[Zn+2].[C-]#N.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>[C:27]([C:7]1[C:17]2[O:16][CH2:15][CH2:14][N:13]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)#[N:28]

참가 물질

7

반응물 2

HCID 6228DimethylformamideHCID 594035221,1-Dimethylethyl 9-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

생성물 1

HCID 54757009Tert-butyl 9-cyano-2,3-dihydrobenzo[F][1,4]oxazepine-4(5H)-carboxylate

시약·촉매·용매 4

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 1,1-dimethylethyl 9-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (Preparation 63) (9 g, 22.65 mmol), zinc cyanide (3.99 g, 34.0 mmol) and tetrakis(triphenylphosphine)palladium(0) (2.62 g, 2.265 mmol) in DMF (90 ml) was heated at 80° C. for 24 hrs. The reaction was cooled, diluted with EtOAc (400 ml) and water (400 ml) and filtered to remove insoluble material. The filtrate was separated and the organic layer washed with water, dried over magnesium sulphate and evaporated. Purified by flash chromatography eluting with EtOAc/iso-hexane 1:9 then 1:3 to give the title compound (5.1 g) as a colourless oil. MS (ES): C15H18N2O3 requires 274; found 174 [M+H−100]+.

후처리

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. customto remove insoluble material
  4. customThe filtrate was separated
  5. washthe organic layer washed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customPurified by flash chromatography
  9. washeluting with EtOAc/iso-hexane 1:9

출처 및 근거

ORD 기록
ord-f32031c2f2da41bf85ab343fa26c23b5
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222245B2

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