Acetic Acid → HCID 68543913, compound

HRID 2242916Notes

Reaction equation

HRID 2242916 reaction equation
[C:1]([NH:3][CH3:4])#[CH:2].[Cl:5][C:6]1[C:11]([CH:12]=O)=[C:10]([F:14])[C:9]([CH3:15])=[CH:8][CH:7]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[Cl:5][C:6]1[C:11]([CH2:12][N:3]([C:1]#[CH:2])[CH3:4])=[C:10]([F:14])[C:9]([CH3:15])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 12682786-Chloro-2-fluoro-3-methylbenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 22945101HCID 22945101, compound

Product 1

HCID 68543913HCID 68543913, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethynyl-methylamine (98 uL, 1.16 mmol) and 6-chloro-2-fluoro-3-methyl-benzaldehyde (200 mg, 1.16 mmol) in CH2Cl2 (3 mL) was added sodium triacetoxyborohydride (369 mg, 1.74 mmol) and acetic acid (7 uL, 0.12 mmol). The reaction mixture was stirred at room temperature for 2 hours, quenched with saturated aqueous NaHCO3, and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, and concentrated to afford the title compound as yellow oil.

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b6d175634c4f44cca56e58963d37d3f5
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

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