Sodium borohydride → HCID 22612319, compound

HRID 844073Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([C:12]1[C:13]([O:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:11].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH:10]([C:12]1[C:13]([O:18][C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)=[N:14][CH:15]=[CH:16][CH:17]=1)[OH:11]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 76.0 mg (0.214 mmol) 3-(2-Chlorophenyl)-1-[2-(4-fluorophenoxy)-3-pyridinyl]-1-propanone in 5 mL of methanol was cooled to 0° C. and treated with 8.0 mg (0.21 mmol) of NaBH4. The mixture was stirred for 30 min at 0° C. and quenched by the addition of 1 mL of aqueous 1 N hydrochloric acid solution. The mixture was evaporated, and the residue was partitioned between 100 mL of EtOAc and 50 mL of saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with brine, dried (Na2SO4), and evaporated to give 79 mg (100%) of the title compound as an oil. 1H NMR (CDCl3) d 2.10-2.32 (2H, m), 2.35 (1H, d, J=6 Hz), 2.83-3.08 (2H, m), 5.06-5.15 (1H, m), 7.01-7.33 (9H, m), 7.85 (1H, dd, J=2, 7 Hz), 8.05 (1H, dd, J=2, 5 Hz); thermospray MS (m/e) 358 and 360 (M++1).

Workup

customquenched by the addition of 1 mL of aqueous 1 N hydrochloric acid solution
customThe mixture was evaporated
customthe residue was partitioned between 100 mL of EtOAc and 50 mL of saturated aqueous sodium hydrogencarbonate solution
washThe organic layer was washed with brine
dry with materialdried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-921f998eb6a4404db2c125f1bf835035
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380218B1

Reaction notes

Loading…