Sodium borohydride → HCID 9820932, compound

HRID 566440Notes

Reaction equation

HRID 566440 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:20](=[O:21])[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH:12]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[F:28][C:25]1[CH:24]=[CH:23][C:22]([N:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][N:15]=3)[C:20](=[O:21])[C:11]([CH2:10][C:7]3[CH:6]=[CH:5][C:4]([CH:1]([OH:3])[CH3:2])=[CH:9][CH:8]=3)=[CH:12]2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 9820812HCID 9820812, compound

Product 1

HCID 9820932HCID 9820932, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 49 mg (0.13 mmol) of the compound of Example 7 in 7 mL of methanol was cooled to 0° C. and treated with 5.0 mg (0.13 mmol) of sodium borohydride. After stirring for 1 hour at 0° C. and 2 hours at room temperature, the mixture was quenched by the addition of 2 mL of water. The mixture was concentrated to remove methanol and the residue was partitioned between 50 mL of ethyl acetate and 50 mL of water. The separated organic layer was washed with brine (1×50 mL), dried (MgSO4), and evaporated to give 22 mg of the title compound as a white solid, mp 197-198° C. Anal. Calcd for C23H19N2O2F: C, 73.78; H, 5.11; N, 7.48. Found: C, 73.41; H, 5.20; N, 7.41.

Workup

  1. customthe mixture was quenched by the addition of 2 mL of water
  2. concentrationThe mixture was concentrated
  3. customto remove methanol
  4. customthe residue was partitioned between 50 mL of ethyl acetate and 50 mL of water
  5. washThe separated organic layer was washed with brine (1×50 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-a0ad30f228904be7aba96fdde5e1ce0f
Source dataset
uspto-grants-2001_01
Patent number
US06174895B1

Reaction notes

Loading…