Methanol → tert-Butyl 5-phenylpyridin-2-ylcarbamate

HRID 2221086Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.CO.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[C:18]1([C:2]2[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 1B (7.65 g, 28 mmol) in THF (50 mL)-MeOH (50 mL) at RT was added phenylboronic acid (6.83 g, 56 mmol), PXPd (500 mg, 0.93 mmol), followed by K2CO3 (15.5 g, 112 mmol). The reaction mixture was stirred at 70° C. in a preheated oil bath for 1 h. After this time, the reaction mixture was cooled to RT. The reaction mixture was poured into water (100 mL), and the resultant mixture was extracted with EtOAc (3×100 mL). The combined organic layers were washed with saturated NaCl. The organic layer was dried (Na2SO4), filtered and concentrated. The resulting residue was purified by silica gel (120 g) column chromatography eluting with a gradient of EtOAc (0-60%) in hexane to give the title compound as an off-white solid (5.4 g, 72%). LC/MS (method A): retention time=3.07 min, (M+H)+=271.

Workup

temperatureAfter this time, the reaction mixture was cooled to RT
extractionthe resultant mixture was extracted with EtOAc (3×100 mL)
washThe combined organic layers were washed with saturated NaCl
dry with materialThe organic layer was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe resulting residue was purified by silica gel (120 g) column chromatography
washeluting with a gradient of EtOAc (0-60%) in hexane

Sources & evidence

ORD record: ord-89b5d69a5aa34010b45e5ccad462765b
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368458B2

Reaction notes

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