Allyl bromide → methyl 2-[2-(allyloxy)phenyl]-3-cyclohexyl-1H-indole-6-carboxylate

HRID 1669468Notes

Reaction equation

[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[OH:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[CH2:33](Br)[CH:34]=[CH2:35]>CC#N.C(Cl)Cl>[CH2:35]([O:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:8]1[NH:9][C:10]2[C:15]([C:7]=1[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[CH:14][CH:13]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:11]=2)[CH:34]=[CH2:33]

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1H-indole-6-carboxylate (prepared as described in published International patent application WO 2006/046030) was suspended in MeCN/DCM (1:1, 0.1M) and K2CO3 (1 eq) was added. To the stirred mixture allyl bromide (1.1 eq) was added and the mixture was warmed to 50° C. After 4 h a further 0.5 eq of allyl bromide were added and heating was continued over night. The mixture was filtered and the filter cake was extracted with hot ethyl acetate. The combined filtrates were evaporated in vacuo. The residual material was dissolved in hot DCM and precipitated by addition of PE. The precipitate was collected and dried in vacuo. The product was obtained as a beige crystalline powder. (81%). (ES+) m/z 390 (M+H)+.

Workup

temperatureheating
waitwas continued over night
filtrationThe mixture was filtered
extractionthe filter cake was extracted with hot ethyl acetate
customThe combined filtrates were evaporated in vacuo
dissolutionThe residual material was dissolved in hot DCM
customprecipitated by addition of PE
customThe precipitate was collected
customdried in vacuo
customThe product was obtained as a beige crystalline powder

Sources & evidence

ORD record: ord-9e3f3eed96674a99b5c2614adacd1651
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989438B2

Reaction notes

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