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

HRID 421941ノート

反応式

HRID 421941 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-9ff26440d4e44c6f96d59fbb251938f3
出典データセット
uspto-grants-2012_01
特許番号
US08101595B2

反応ノート

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