(2-Bromoethoxy)-tert-butyldimethylsilane → HCID 21192931, compound

HRID 1067291Notes

Reaction equation

[Cl:1][C:2]1[C:3]([NH:12][C:13](=[O:26])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:15]=2)=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][NH:9][CH2:8][CH2:7]2.Br[CH2:28][CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>CN(C)C=O>[Si:31]([O:30][CH2:29][CH2:28][N:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:2]([Cl:1])[C:3]([NH:12][C:13](=[O:26])[C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([C:22]([F:23])([F:24])[F:25])[CH:15]=3)=[CH:4][CH:5]=2)[CH2:10]1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-(8-chloro-1,2,3,4-tetrahydroisoquinolin-7-yl)-4-methoxy-3-trifluoromethylbenzamide (0.192 g) and 2-bromoethoxy-tert-butyldimethylsilane (0.24 g) were combined in dimethylformamide and warmed to 80° C. for 18 h. Solvent was removed at reduced pressure, the residue dissolved in dichloromethane and washed with saturated sodium hydrogen carbonate. The organic phase was dried (MgSO4) and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, ammonia/methanol/dichloromethane mixtures as eluant) to give N-(2-(2-tert-butyldimethylsilyloxyethyl)-8-chloro-1,2,3,4-tetrahydroisoquinolin-7-yl)-4-methoxy-3-trifluoromethylbenzamide (0.09 g)

Workup

customSolvent was removed at reduced pressure
dissolutionthe residue dissolved in dichloromethane
washwashed with saturated sodium hydrogen carbonate
dry with materialThe organic phase was dried (MgSO4) and solvent
customremoved at reduced pressure
customchromatographed (silica gel, ammonia/methanol/dichloromethane mixtures as eluant)

Sources & evidence

ORD record: ord-e50bc60c11c840608fa13ee7690351e8
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248754B1

Reaction notes

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