Trityl chloride → HCID 67994874, compound

HRID 2361421Notes

Reaction equation

HRID 2361421 reaction equation
[Br:1][C:2]1[C:10]2[NH:9][C:8]3[CH2:11][CH2:12][NH:13][CH2:14][C:7]=3[C:6]=2[C:5]([Br:15])=[CH:4][CH:3]=1.[C:16](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[C:10]2[NH:9][C:8]3[CH2:11][CH2:12][N:13]([C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:14][C:7]=3[C:6]=2[C:5]([Br:15])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6456Trityl chlorideHCID 67995387HCID 67995387, compound

Product 1

HCID 67994874HCID 67994874, compoundYield 114.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 6,9-dibromo-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (700 mg, 2.121 mmol) in dichloromethane (10 mL) was stirred on an ice-water bath and treated with TEA (0.591 mL, 4.24 mmol), DMAP (25.9 mg, 0.212 mmol) and trityl chloride (1.183 g, 4.24 mmol). The mixture was allowed to warmed to room temperature and stirred for 71 h. The solution was concentrated under vacuum and the residue was subjected to column chromatography on silica gel (120 g), eluting with EtOAc-hexane (gradient from 5:95 to 50:50) to provide the desired product as a yellow glassy foam (1.388 g) contaminated with a trityl derivative (probably trityl chloride or triphenylmethanol), estimated purity 75% (estimated yield of desired product 82%). This material was used without further purification. LCMS m/z 243.2 (trityl cation), 329, 331, 333 (M+H-trityl)+.

Workup

  1. stirringstirred for 71 h
  2. concentrationThe solution was concentrated under vacuum
  3. washeluting with EtOAc-hexane (gradient from 5:95 to 50:50)

Sources & evidence

ORD record
ord-04134d3267f84f08806507f37603eb9a
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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