Tetrahydrofuran → HCID 57707799, compound

HRID 216850Notes

Reaction equation

HRID 216850 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[C:19]([F:22])([F:21])[F:20])[C:8]([CH:23]=[O:24])=[CH:7]2.O1CCCC1.[BH4-].[Na+]>>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[C:19]([F:22])([F:20])[F:21])[C:8]([CH2:23][OH:24])=[CH:7]2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 577078688-Chloro-2-(5-fluoro-2-(trifluoromethyl)phenyl)quinoline-3-carbaldehyde

Product 1

HCID 57707799HCID 57707799, compound

Conditions

Temperature
0 °C

Procedure

To a solution of 8-chloro-2-(5-fluoro-2-(trifluoromethyl)phenyl)quinoline-3-carbaldehyde (0.3036 g, 0.8584 mmol) in tetrahydrofuran (4.292 mL, 0.8584 mmol) at 0° C. was added sodium borohydride (0.04871 g, 1.288 mmol) and the mixture was stirred at 0° C. After 1 h of stirring at 0° C., the mixture was partitioned between EtOAc (100 mL) and H2O (100 mL), and the organic layer was washed with brine (50 mL×2), dried over Na2SO4, filtered, and concentrated under reduced pressure to give (8-chloro-2-(5-fluoro-2-(trifluoromethyl)phenyl)-quinolin-3-yl)methanol as a light-yellow syrupy solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.57 (1H, s), 8.10 (1H, dd, J=8.2, 1.2 Hz), 8.01 (1H, dd, J=8.8, 5.3 Hz), 7.95 (1H, dd, J=7.6, 1.4 Hz), 7.53-7.69 (3H, m), 5.55 (1H, br. s.), 4.25-4.56 (2H, m); LC-MS (ESI) m/z 356.0 [M+H]+. The light-yellow syrupy solid was carried on crude without purification for the next step.

Workup

  1. stirringAfter 1 h of stirring at 0° C.
  2. customthe mixture was partitioned between EtOAc (100 mL) and H2O (100 mL)
  3. washthe organic layer was washed with brine (50 mL×2)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d39a85ee15e4170a46fa24719300b27
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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