Lithium borohydride → HCID 86301335, compound

HRID 1748389Notes

Reaction equation

HRID 1748389 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([C:18](=[O:20])[CH3:19])[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].[Li+].[BH4-]>C1COCC1>[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([CH:18]([OH:20])[CH3:19])[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4148881Lithium borohydrideHCID 4311764Sodium borohydride2×HCID 86301334HCID 86301334, compound

Product 1

HCID 86301335HCID 86301335, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution, 0° C., of 1-(7-((4-fluorobenzyl)oxy)quinolin-3-yl)ethanone (Example 42, 53 mg, 0.18 mmol) in THF was added NaBH4 (8 mg, 0.24 mmol). The reaction mixture was stirred for 1 hour. A further portion of NaBH4 (20 mg, 0.59 mmol) was added and stirred for 30 minutes at 0° C. LiBH4 (50 mg, 2.30 mmol) was added and the reaction was stirred for 15 minutes before being quenched with sat. NH4Cl (aq.) solution. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine and concentrated under reduced pressure onto silica. Purification (FCC, SiO2, 0-5%, MeOH/DCM) afforded the title compound as a white solid (20 mg, 38%). 1H NMR (400 MHz, CDCl3) δ 8.85 (d, J=1.6 Hz, 1H), 8.10 (s, 1H), 7.73 (d, J=9.0 Hz, 1H), 7.53-7.43 (m, 3H), 7.31-7.26 (m, 1H), 7.09 (t, J=8.6 Hz, 2H), 5.17 (s, 2H), 5.12 (q, J=6.5 Hz, 1H), 1.62 (d, J=6.7 Hz, 3H). [M+H]=298.3.

Workup

  1. stirringstirred for 30 minutes at 0° C
  2. stirringthe reaction was stirred for 15 minutes
  3. custombefore being quenched with sat. NH4Cl (aq.) solution
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. concentrationconcentrated under reduced pressure onto silica
  7. customPurification (FCC, SiO2, 0-5%, MeOH/DCM)

Sources & evidence

ORD record
ord-a3f613f9d86448b3bbd1a1da5f7be4ce
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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