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

HRID 421941
Notes
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Reaction equation

HRID 421941 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-9ff26440d4e44c6f96d59fbb251938f3
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08101595B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes