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

HRID 421941Notes

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

Participants

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

temperatureto cool to RT
customVolatiles were removed in vacuo
additiondiluted with EtOAc
washwashed with water
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
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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