Methyl 2-chloroacrylate → Dimethyl 13-cyclohexyl-6,7-dihydroindolo[1,2-d][1,4]benzoxazepine-6,10-dicarboxylate

HRID 421941

반응식

HRID 421941 반응식
Cl[C:2](=[CH2:7])[C:3]([O:5][CH3:6])=[O:4].[Cl-].C([N+](CC)(CC)CCCC)C.C([O-])([O-])=O.[K+].[K+].[CH:26]1([C:32]2[C:40]3[C:35](=[CH:36][C:37]([C:41]([O:43][CH3:44])=[O:42])=[CH:38][CH:39]=3)[NH:34][C:33]=2[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[OH:51])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>CC#N>[CH:26]1([C:32]2[C:40]3[CH:39]=[CH:38][C:37]([C:41]([O:43][CH3:44])=[O:42])=[CH:36][C:35]=3[N:34]3[C:33]=2[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[O:51][CH:2]([C:3]([O:5][CH3:6])=[O:4])[CH2:7]3)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1

참가 물질

6

반응물 4

HCID 6659Methyl 2-chloroacrylateHCID 11430Potassium CarbonateHCID 10888803N-ButyltriethylammoniumchlorideHCID 11995228Methyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1H-indole-6-carboxylate

생성물 1

HCID 66674678Dimethyl 13-cyclohexyl-6,7-dihydroindolo[1,2-d][1,4]benzoxazepine-6,10-dicarboxylate수율 81%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

Methyl chloroacrylate (1.7 eq.), triethylbutyl ammonium chloride (0.2 eq.) and K2CO3 (6 eq.) were added to a solution of methyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1H-indole-6-carboxylate (prepared as described in International patent application publication W02006/046030, Example 9) in anhydrous MeCN (0.02 M). The mixture was heated at 60° C. overnight and then allowed to cool to RT. Volatiles were removed in vacuo, diluted with EtOAc, washed with water, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by FC (EtOAc/PE 10:90) to afford the product as a solid (81%). (ES+) m/z 434 (M+H)+.

후처리

  1. temperatureto cool to RT
  2. customVolatiles were removed in vacuo
  3. additiondiluted with EtOAc
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by FC (EtOAc/PE 10:90)

출처 및 근거

ORD 기록
ord-9ff26440d4e44c6f96d59fbb251938f3
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101595B2

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