(3-Bromopropyl)benzene → HCID 86753862, compound

HRID 1417969Notes

Reaction equation

HRID 1417969 reaction equation
CC([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])C.[C:31]1([CH2:37][CH2:38][CH2:39]Br)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[H-].[Na+].C[O:44][C:45](C)([CH3:47])[CH3:46]>CN(C)C=O>[CH2:19]([O:18][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[C:9]1[C:8]([CH2:28][O:29][CH3:30])=[C:7]([C:5]([OH:4])=[O:6])[N:27]=[CH:26][C:10]=1[N:11]2[CH2:39][CH2:38][CH2:37][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:46][CH:45]([O:44][CH:38]([CH3:37])[CH3:39])[CH3:47]

Participants

6

Reactant 4

HCID 12503(3-Bromopropyl)benzeneHCID 15413tert-Butyl methyl etherHCID 24758Sodium hydrideHCID 541385905-Benzyloxy-4-methoxymethyl-betacarboline-3-carboxylic acid isopropyl ester

Product 1

HCID 86753862HCID 86753862, compound

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 20 ml of dimethylformamide, mixed with 597 mg of 3-phenylpropyl bromide and 40 mg of sodium hydride (60% suspension in oil), and it is stirred for one hour at room temperature. 300 ml of methyl-tert-butyl ether is added to the reaction mixture, and the organic phase is washed with 20% citric acid and saturated sodium chloride solution. The organic phase is dried on sodium sulfate and evaporated to dryness in a vacuum. The crude product that is obtained is purified on a silica gel column with ethyl acetate-hexane, and 338 mg of 5-benzyloxy-4-methoxymethyl-9-(3-phenylpropyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ether is obtained.

Workup

  1. washthe organic phase is washed with 20% citric acid and saturated sodium chloride solution
  2. customThe organic phase is dried on sodium sulfate
  3. customevaporated to dryness in a vacuum
  4. customThe crude product that is obtained
  5. customis purified on a silica gel column with ethyl acetate-hexane

Sources & evidence

ORD record
ord-f8dd79b846df48659a4e4a5da558e691
Source dataset
uspto-grants-1999_03
Patent number
US05880126

Reaction notes

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