3-(3-Methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)isonicotinaldehyde → 5-(4-(1-hydroxypropyl)pyridin-3-yl)-3-methylbenzo[d]oxazol-2(3H)-one

HRID 1253942Notes

Reaction equation

HRID 1253942 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][N:6]1[C:10]2[CH:11]=[C:12]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][C:20]=3[CH:21]=[O:22])[CH:13]=[CH:14][C:9]=2[O:8][C:7]1=[O:23]>C1COCC1>[OH:22][CH:21]([C:20]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[C:12]1[CH:13]=[CH:14][C:9]2[O:8][C:7](=[O:23])[N:6]([CH3:5])[C:10]=2[CH:11]=1)[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 866633583-(3-Methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)isonicotinaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 667980145-(4-(1-hydroxypropyl)pyridin-3-yl)-3-methylbenzo[d]oxazol-2(3H)-oneYield 7.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethylmagnesium bromide (3 M in THF, 0295 mL, 0.885 mmol) was added dropwise to a solution of 3-(3-Methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-pyridine-4-carbaldehyde (75 mg, 0.295 mmol) in THF (2 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 reverse phase chromatography (10%-100%, v/v, ACN-water), 6 mg of desired product was obtained. ESI-MS m/z: 285.1 [M+1]+, Retention time 1.00 min; 1HNMR (CDCl3, 400.342 MHz) δ ppm 0.74 (t, J=7.3 Hz, 3H), 1.47-1.53 (m, 2H), 3.40 (s, 3H), 4.93 (t, J=5.5 Hz, 1H), 7.03 (dd, J=8.1, 1.2 Hz, 1H), 7.16 (s, 1H), 7.25 (d, J=8.1 Hz, 1H), 8.03 (d, J=5 Hz, 1H), 8.36 (s, 1H), 8.52 (d, J=5 Hz, 1H).

Workup

  1. customthe reaction was quenched by the addition of saturated NH4Cl solution
  2. additionThe mixture was diluted with ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe residue was purified by reverse phase chromatography (10%-100%, v/v, ACN-water)

Sources & evidence

ORD record
ord-b192ed3273ce40c0b31cfc16303035c0
Source dataset
uspto-grants-2013_06
Patent number
US08455522B2

Reaction notes

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