Formic Acid → HCID 59526060, compound

HRID 385797Notes

Reaction equation

HRID 385797 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:16])[CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C(O)=O>CO.C(OCC)(=O)C.C(=O)(O)[O-].[Na+].O>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:16])[CH2:9][N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 284Formic AcidHCID 4311764Sodium borohydrideHCID 595263201-(6-Bromopyridin-2-yl)-2-morpholin-4-ylethanone

Product 1

HCID 59526060HCID 59526060, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1-(6-bromopyridin-2-yl)-2-morpholin-4-ylethanone (234 mg, 0.82 mmol) in methanol at 0° C. was added sodium borohydride (31.0 mg, 0.82 mmol). After 30 minutes, formic acid (0.1 mL) was added and then the reaction mixture was diluted with ethyl acetate (40 mL), saturated aqueous sodium bicarbonate (10 mL), and water (10 mL). The layers were separated and the organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered, and concentrated to give the title compound.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with brine (10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c55cd15ae1fc47f487154705eca98c17
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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