3-(3-Methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)isonicotinaldehyde → 5-(4-(cyclopropyl(hydroxy)methyl)pyridin-3-yl)-3-methylbenzo[d]oxazol-2(3H)-one
Reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[CH3:6][N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:21]=3[CH:22]=[O:23])[CH:14]=[CH:15][C:10]=2[O:9][C:8]1=[O:24]>C1COCC1>[CH:1]1([CH:22]([OH:23])[C:21]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[C:13]2[CH:14]=[CH:15][C:10]3[O:9][C:8](=[O:24])[N:7]([CH3:6])[C:11]=3[CH:12]=2)[CH2:3][CH2:2]1Participants
4
Procedure
Cyclopropylmagnesium bromide (0.5 M in THF, 3.5 mL, 1.8 mmol) was added dropwise to a solution of 3-(3-Methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-pyridine-4-carbaldehyde (150 mg, 0.58 mmol) in THF (1.6 mL) at −36′C. The resulting mixture was stirred at this temperature for 3 h, and the reaction was quenched by the addition of saturated NH4Cl solution. The mixture was diluted with ethyl acetate and water. The organic layer was separated and dried over anhydrous Na2SO4. After filtration and concentration, the residue was purified by flash column (MeOH/DCM, v/v, 0-4%) to give the title compound. (67 mg, 39%); ESI-MS m/z 297.2 [M+1]+, Retention time 1.00 min; 1HNMR (CDCl3, 400.342 MHz) δ ppm −0.27-0 (m, 1H), 0.36-0.45 (m, 2H), 0.52-0.57 (m, 1H), 0.96-1.02 (m, 1H), 3.47 (s, 3H), 4.52 (d, J=7.6 Hz, 1H), 7.14 (dd, J=8, 1.6 Hz, 1H), 7.25 (d, J=1.6 Hz, 1H), 7.33 (d, J=: 8 Hz, 1H), 8.18 (d, J=6 Hz, 1H), 8.47 (s, 1H), 8.63 (d, J=6 Hz, 1H).