Lithium borohydride → HCID 11475591, compound

HRID 1866896Notes

Reaction equation

[Br:1][C:2]1[C:3](=[O:28])[N:4]([CH2:17][C:18]2[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=2[C:20](OC)=[O:21])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1.[Li+].[BH4-]>C1COCC1>[Br:1][C:2]1[C:3](=[O:28])[N:4]([CH2:17][C:18]2[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=2[CH2:20][OH:21])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To an ice-cold solution of 3-bromo-4-(4-fluorobenzyloxy)-1-(2-hydroxymethylbenzyl)-1H-pyridin-2-one (Example 72) (0.25 g, 0.56 mmol) in THF (1 mL) was added LiBH4 (2.0 M solution in THF, 0.56 mmol), and the reaction mixture was stirred at 40° C. for 6 hours. The reaction mixture was cooled to room temperature, the solvent was removed under reduced pressure, and the residue was dissolved in EtOAc. The organic solution was washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. 1H NMR (300 MHz, DMSO-d6) δ 7.82 (d, J=8 Hz, 1H), 7.54-7.49 (m, 2H), 7.41 (d, J=7 Hz, 1H), 7.29-7.21 (m, 4H), 6.81 (d, J=7 Hz, 1H), 6.53 (d, J=8 Hz, 1H), 5.30-5.25 (m, 3H), 5.18 (s, 2H), 4.60 (d, J=7 Hz, 2H). ESHRMS m/z 418.0437 (M+H C20H18BrFNO3 requires 418.0449)

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe solvent was removed under reduced pressure
dissolutionthe residue was dissolved in EtOAc
washThe organic solution was washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-95380c312aa043cfadeb003ac980dce5
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629363B2

Reaction notes

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