Sodium borohydride → HCID 21865094, compound

HRID 858996Notes

Reaction equation

HRID 858996 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][N:12]=[C:11]([O:15][C:16]3[CH:17]=[CH:18][CH:19]=[C:20]4[C:25]=3[NH:24][C:23](=[O:26])[CH:22]=[N:21]4)[CH:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+]>CCO>[F:27][C:2]([F:1])([F:28])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][N:12]=[C:11]([O:15][C:16]3[CH:17]=[CH:18][CH:19]=[C:20]4[C:25]=3[NH:24][C:23](=[O:26])[CH2:22][NH:21]4)[CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21865040HCID 21865040, compound

Product 1

HCID 21865094HCID 21865094, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 8-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-1H-quinoxalin-2-one, (Example 32(e)), (0.25 g, 0.65 mmol) in EtOH (5 mL) was added sodium borohydride (0.11 mg, 2.8 mmol, Aldrich). After stirring at room temperature for 2 h, the mixture was quenched with satd aq. NaHCO3 and extracted with 25% i-PrOH/CHCl3 (3×). The combined organic layers were dried over Na2SO4, filtered and concentrated. Purification by flash chromatography (0→1.5% 2M NH3/MeOH in CH2Cl2) gave the title compound as a light-yellow powder. Mp: 305° C., MS (ESI, pos. ion) m/z: 387 (M+1).

Workup

  1. customthe mixture was quenched with satd aq. NaHCO3
  2. extractionextracted with 25% i-PrOH/CHCl3 (3×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (0→1.5% 2M NH3/MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-53197574cab74dc6a59f96096b6f369d
Source dataset
uspto-grants-2006_12
Patent number
US07148221B2

Reaction notes

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