1-Propanol → 6,6-Dimethyl-11-oxo-8-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61754

반응식

HRID 61754 반응식
[C:1]([C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[C:8](=[O:30])[C:9]4[CH:21]=[CH:20][C:19](OS(C(F)(F)F)(=O)=O)=[CH:18][C:10]=4[C:11]([CH3:17])([CH3:16])[C:12]=3[NH:13]2)=[CH:5][CH:4]=1)#[N:2].[CH2:31](O)[CH2:32]C.C([B-](F)(F)F)=C.[K+].C(N(CC)CC)C>O>[CH3:16][C:11]1([CH3:17])[C:12]2[NH:13][C:14]3[C:6](=[CH:5][CH:4]=[C:3]([C:1]#[N:2])[CH:15]=3)[C:7]=2[C:8](=[O:30])[C:9]2[CH:21]=[CH:20][C:19]([CH:31]=[CH2:32])=[CH:18][C:10]1=2

참가 물질

6

반응물 4

HCID 10311-PropanolHCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 86663817Trifluoro-methanesulfonic acid 3-cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yl ester2회

생성물 1

HCID 668340546,6-Dimethyl-11-oxo-8-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile수율 80%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

Under nitrogen atmosphere, trifluoro-methanesulfonic acid 3-cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yl ester (Compound B1, 1.00 g, 2.302 mmol) was added with n-propanol (20 mL), potassium vinyltrifluoroborate (854 mg, 3.0 eq.), dichloro-((bis-diphenylphosphino)ferrocenyl)palladium (217 mg, 0.1 eq.) and triethylamine (1.11 ml, 3.0 eq.) in order and the resultant was stirred at 60° C. for 4 hr. Upon the completion of the reaction, water was added to the reaction solution. The resulting precipitates were filtered and washed with distilled water, and the residues were dried to obtain the title compound (666 mg, 80%).

후처리

  1. additionwas added to the reaction solution
  2. customThe resulting precipitates
  3. filtrationwere filtered
  4. washwashed with distilled water
  5. customthe residues were dried

출처 및 근거

ORD 기록
ord-27637dfe19f8455bb26f5e4928000c58
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440922B2

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