Sodium borohydride → HCID 57707816, compound

HRID 1397773Notes

Reaction equation

HRID 1397773 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-e33ffb9803da4c8580c8c85e99f67830
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

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