Sodium borohydride → 5-(5-fluoro-4-(hydroxymethyl)pyridin-3-yl)-3-methylbenzo[d]oxazol-2(3H)-one

HRID 1253949Notes

Reaction equation

HRID 1253949 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([C:12]2[CH:13]=[CH:14][C:15]3[O:19][C:18](=[O:20])[N:17]([CH3:21])[C:16]=3[CH:22]=2)[C:9]=1[CH:10]=[O:11]>C1COCC1.O.[Cl-].[Na+].O.C(Cl)Cl>[F:3][C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:12]2[CH:13]=[CH:14][C:15]3[O:19][C:18](=[O:20])[N:17]([CH3:21])[C:16]=3[CH:22]=2)[CH:7]=[N:6][CH:5]=1

Participants

7

Reactant 2

HCID 4311764Sodium borohydrideHCID 86663361HCID 86663361, compound

Product 1

HCID 667977725-(5-fluoro-4-(hydroxymethyl)pyridin-3-yl)-3-methylbenzo[d]oxazol-2(3H)-oneYield 16%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium borohydride (6.3 mg, 0.17 mmol) was added to a solution of 3-Fluoro-5-(3-methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-pyridine-4-carbaldehyde (47 mg, 0.17 mmol) in THF (0.5 mL) and water (0.1 mL) at 0° C. The resulting mixture was stirred at room temperature for 2 h. Brine was added to the reaction mixture. The resulting mixture was diluted with DCM and water. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column (MeOH—CH2Cl2, v/v, 0-3%) and afforded the title compound (7 mg, 16%); ESI-MS m/z: 275 [M+1]+, Retention time 0.92 min; 1HNMR (MeOD, 400.3 MHz) δ 3.44 (s, 3H), 4.59 (s, 2H), 7.32 (dd, J=8.0, 1.2 Hz, 1H), 7.35 (d, J=1.2 Hz, 1H), 7.38 (d, J=80 Hz, 1H), 8.39 (s, 1H), 8.48 (d, J=1.2 Hz, 1H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash column (MeOH—CH2Cl2, v/v, 0-3%)

Sources & evidence

ORD record
ord-c23cc2869bba4fd9bb134b68721492e7
Source dataset
uspto-grants-2013_06
Patent number
US08455522B2

Reaction notes

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