Benzyl Bromide → HCID 44213509, compound

HRID 1417973Notes

Reaction equation

HRID 1417973 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)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(=O)([O-])[O-].[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]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=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 7498Benzyl BromideHCID 10796Cesium carbonateHCID 541385905-Benzyloxy-4-methoxymethyl-betacarboline-3-carboxylic acid isopropyl ester

Product 1

HCID 44213509HCID 44213509, compoundYield 39.2%

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 188 mg (1.1 mmol) of benzyl bromide and 358 mg of cesium carbonate. It is stirred for 48 hours at room temperature, the reaction mixture s worked up as described in Example 26, and after chromatography, 194 mg of 5-benzyloxy-4-methoxymethyl-9-benzyl-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester is obtained.

Sources & evidence

ORD record
ord-72d86b6eef444c2ba21ce5b5a14e4b8d
Source dataset
uspto-grants-1999_03
Patent number
US05880126

Reaction notes

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