Lithium borohydride → HCID 11475591, compound

HRID 1831912Notes

Reaction equation

HRID 1831912 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

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 11247821HCID 11247821, compound

Product 1

HCID 11475591HCID 11475591, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 concemtrated 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). ES HRMS m/z 418.0437 (M+H C20H18BrFNO3 requires 418.0449).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in EtOAc
  4. washThe organic solution was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-dd1d99b420ab4cb18e3db31e28c2b767
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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