Sodium hydride → [3-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-pyridin-3-yl-amine

HRID 1784827Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([OH:15])[CH:5]=[C:6]([NH:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:7]=1.[H-].[Na+].[Si:18](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C.C(OC)(C)(C)C>[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:5]=[C:4]([O:15][Si:18]([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-Bromo-5-(pyridin-3-ylamino)-phenol (11.62 g, 43.83 mmol) was dissolved in DMF (115 mL) under dry argon and cooled to 0° C. Then 60% NaH (1.93 g, 48.21 mmol) was added in small portions over a period of 45 min. Stirring was continued for 15 min, followed by drop wise addition of TBDPS-chloride (11.2 mL, 43.83 mmol). The mixture was warmed to room temperature and stirred for 20 h. The reaction mixture was diluted with tert-butylmethyl ether (200 mL) and washed with water and brine (2×50 mL each). The organic layer was dried (MgSO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (600 g, AcOEt/heptane 1:2→1:1). [3-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-pyridin-3-yl-amine (21.2 g, 96%) was obtained as a yellow resin.

Workup

temperatureThe mixture was warmed to room temperature
stirringstirred for 20 h
washwashed with water and brine (2×50 mL each)
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated
customto give the crude product which
customwas purified by flash chromatography on silica gel (600 g, AcOEt/heptane 1:2→1:1)

Sources & evidence

ORD record: ord-c98fbd1f4a384f9ea983660d178fffc7
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504401B2

Reaction notes

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