Methanol → tert-Butyl (6-phenylpyridin-3-yl)carbamate

HRID 2221093Notes

Reaction equation

Br[C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=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[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 3A (8.3 g, 30.3 mmol) in THF (50 mL)-MeOH (50 mL) at RT was added phenylboronic acid (7.44 g, 61 mmol), PXPd (489 mg, 0.91 mmol), followed by K2CO3 (16.75 g, 121 mmol). The reaction mixture was stirred at 70° C. in a preheated oil bath for lh. 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 organics were washed with saturated NaCl, dried (Na2SO4), filtered and concentrated. The resulting residue was triturated with 30% EtOAc in hexane. The solid was collected by filtration to give the title compound as an off-white solid (5.6 g, 68%). LC/MS (method A): retention time=2.83 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 organics were washed with saturated NaCl
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe resulting residue was triturated with 30% EtOAc in hexane
filtrationThe solid was collected by filtration

Sources & evidence

ORD record: ord-36dc8e82040d4e22882dc1227f1009de
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368458B2

Reaction notes

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