Cesium carbonate → HCID 67595794, compound

HRID 1417972Notes

Reaction equation

HRID 1417972 reaction equation
[CH3:1][CH:2]([O:4][C:5]([C:7]1[N:27]=[CH:26][C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8]=1[CH2:28][O:29][CH3:30])=[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:15]=[CH:14][CH:13]=3)=[O:6])[CH3:3].[CH2:31](Br)[CH:32]=[CH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(=O)([O-])[O-:42].[Cs+].[Cs+]>CN(C)C=O>[CH3:3][CH:2]([O:4][C:5]([C:7]1[N:27]=[CH:26][C:10]2[N:11]([C:31](=[O:42])[CH:32]=[CH:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:12]3[C:17]([C:9]=2[C:8]=1[CH2:28][O:29][CH3:30])=[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:15]=[CH:14][CH:13]=3)=[O:6])[CH3:1]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 98116BromomethylstyreneHCID 541385905-Benzyloxy-4-methoxymethyl-betacarboline-3-carboxylic acid isopropyl ester

Product 1

HCID 67595794HCID 67595794, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

404.5 mg of 5-benzyloxy-4-methoxymethyl-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester (1 mmol) is dissolved in 15 ml of dimethylformamide and mixed with 217 mg (1.1 mmol) of cinnamyl bromide and 358 mg (1.1 mmol) of cesium carbonate. It is stirred for 48 hours at room temperature, the reaction mixture is worked up, as described in Example 26, and after chromatography, 210 mg of 5-benzyloxy-4-methoxymethyl-9-cinnamoyl-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester is obtained.

Sources & evidence

ORD record
ord-b0e32676b21a485cbe87d5796ac272b4
Source dataset
uspto-grants-1999_03
Patent number
US05880126

Reaction notes

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