Ethyl bromoacetate → HCID 86637916, compound

HRID 2389383Notes

Reaction equation

[C:1]1([CH:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:26])[N:12]([CH2:14]/[CH:15]=[CH:16]/[C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[CH:20][NH:21]4)[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CC(=O)CC.CCOC(C)=O>[C:1]1([CH:7]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:26])[N:12]([CH2:14]/[CH:15]=[CH:16]/[C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[CH:20][N:21]4[CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-(diphenylmethyl)-1-[(2E)-3-(1H-indol-4-yl)-2-propen-1-yl]-2(1H)-pyridinone (80 mg), K2CO3 (80 mg) and benzyltriethylammonium chloride (8.8 mg) in 2-butanone (1 mL) was added ethyl bromoacetate (96 mg) at ambient temperature. The reaction mixture was stirred for 5 hours at 80° C. The resulting mixture was diluted with EtOAc and washed successively with water and brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:MeOH=100:0-97:3) to give ethyl (4-{(1E)-3-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]-1-propen-1-yl}-1H -indol-1-yl)acetate.

Workup

washwashed successively with water and brine
dry with materialThe organic layer was dried over anhydrous MgSO4
filtrationfiltered
customevaporated in vacuo
customThe residue was purified by silica gel column chromatography (chloroform:MeOH=100:0-97:3)

Sources & evidence

ORD record: ord-a0d595fae97a495ab1e960426963b5d8
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273745B2

Reaction notes

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