Sodium Carbonate → 5-(4-acetylpyridin-3-yl)-3-methylbenzo[d]oxazol-2(3H)-one

HRID 1253927Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8](=[O:10])[CH3:9].[CH3:11][N:12]1[C:16]2[CH:17]=[C:18](B3OC(C)(C)C(C)(C)O3)[CH:19]=[CH:20][C:15]=2[O:14][C:13]1=[O:30].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:8]([C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:18]1[CH:19]=[CH:20][C:15]2[O:14][C:13](=[O:30])[N:12]([CH3:11])[C:16]=2[CH:17]=1)(=[O:10])[CH3:9]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1-(3-bromopyridin-4-yl)ethanone (50 mg, 0.250 mmol), 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2(3H)-one (68.8 mg, 0.250 mmol), polymer bound PalladiumTetrakis (56.8 mg, 6.25 μmol) and sodium carbonate (250 μl, 0.500 mmol) in toluene (1 mL) and ethanol (1 mL) was heated to 90° C. in microwave for 45 min. After filtration through a pad of Na2SO4, the solvent was removed in vacuum. The residue was purified by flash column (MeOH—CH2Cl2, v/v, 1%-1.5%) and yielded colorless solid (37 mg). ESI-MS m/z: 269.0 [M+1]+, Retention time 1.03 min; 1H NMR (400.3 MHz, CDCl3): δ 2.13 (s, 3H), 344 (s, 3H), 6.95 (d, J=1.48 Hz, 1H), 7.07 (dd, J=8.2, 1.68 Hz, 1H), 7.29 (d, J=8.2 Hz, 1H), 7.37 (d J=5 Hz, 1H), 8.69 (s, 1H), 8.73 (d, J=5 Hz, 1H).

Workup

filtrationAfter filtration through a pad of Na2SO4
customthe solvent was removed in vacuum
customThe residue was purified by flash column (MeOH—CH2Cl2, v/v, 1%-1.5%)

Sources & evidence

ORD record: ord-c04d8fb8b23f452095a50db93690123c
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455522B2

Reaction notes

Loading…