Sodium borohydride → HCID 57707816, compound

HRID 2044937Notes

Reaction equation

HRID 2044937 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20])[C:10]([CH:21]=[O:22])=[CH:9]2>C1COCC1>[Cl:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20])[C:10]([CH2:21][OH:22])=[CH:9]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57707863HCID 57707863, compound

Product 1

HCID 57707816HCID 57707816, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (0.159 g, 4.20 mmol) was added portion wise to a stirring solution of 8-chloro-2-(2-fluorophenyl)quinoline-3-carbaldehyde (0.800 g, 2.80 mmol) in 15 mL of THF. The reaction stirred at room temperature. After 1.5 h, the mixture was partitioned between water and EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure: LC-MS (ESI) m/z 288.1 [M+H]+. The crude product was carried on crude without purification for the next step.

Workup

  1. customthe mixture was partitioned between water and EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was carried on crude without purification for the next step

Sources & evidence

ORD record
ord-06a17b91c923418ca1a27f37b7cf98ec
Source dataset
uspto-grants-2013_11
Patent number
US08586739B2

Reaction notes

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