Potassium Carbonate → 5'-Oxazol-5-yl-[1,3']bipyridinyl-2-one

HRID 1753774Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2[O:12][CH:11]=[N:10][CH:9]=2)[CH:7]=1.[OH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[O:12]1[C:8]([C:6]2[CH:7]=[C:2]([N:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]3=[O:13])[CH:3]=[N:4][CH:5]=2)=[CH:9][N:10]=[CH:11]1

Participants

Conditions

Temperature: 120 °C

Procedure

To an oven-dried sealed tube containing a solution of 3-bromo-5-oxazol-5-yl-pyridine VIII-a (1.00 g, 4.44 mol) in degassed 1,4-dioxane (20 mL) was added 2-hydroxypyridine (507 mg, 5.33 mmol), K2CO3 (1.23 g, 1.78 mmol), Cut (169 mg, 0.899 mmol) and rac-trans-N,N′-dimethylcyclohexane diamine (280 μL, 1.78 mmol). The tube was flushed with argon and sealed then heated in an oil bath at 120° C. overnight. After cooling to RT, the mixture was filtered and the filter cake washed with 1,4-dioxane. The mixture was evaporated and the residue purified by column chromatography (2% to 5% EtOH in DCM) to give the desired product VIII-b as a beige solid (752 mg, 71%). 1H NMR (300 MHz, DMSO-d6) δ 9.06 (s, 1H), 8.68 (s, 1H), 8.60 (s, 1H), 8.29 (s, 1H), 7.95 (s, 1H), 7.80 (dd, J=6.8, 1.6 Hz, 1H), 7.57 (ddd, J=8.8, 6.6, 1.9 Hz, 1H), 6.54 (d, J=9.2 Hz, 1H), 6.39 (t, J=6.7 Hz, 1H).

Workup

customTo an oven-dried sealed tube
customThe tube was flushed with argon
customsealed
temperatureAfter cooling to RT
filtrationthe mixture was filtered
washthe filter cake washed with 1,4-dioxane
customThe mixture was evaporated
customthe residue purified by column chromatography (2% to 5% EtOH in DCM)

Sources & evidence

ORD record: ord-d02e54551dca44df9a597ba7e4e5861d
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09168245B2

Reaction notes

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