Oxalyl chloride → 2-Methylpyridine-3-carbonyl chloride
Reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:14])=O>C(Cl)Cl.CN(C=O)C>[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:14])=[O:5]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a suspension of methylnicotinic acid (500 mg, 3.6 mmol) in DCM (30 mL) is added oxalyl chloride (0.93 mL, 10.9 mmol) dropwise followed by DMF (1 drop). The reaction mixture is stirred at room temperature for 1 h and then concentrated in vacuo to give methylnicotinoyl chloride in a quantitative yield. A solution of I-83.1 (250 mg, 0.93 mmol) and methylnicotinoyl chloride (159.0 mg, 1.02 mmol) in DCM is stirred at room temperature for 1 h with the addition of more methylnicotinoyl chloride (28.9 mg, 0.19 mmol). The reaction mixture is then diluted with saturated aqueous NaHCO3 and the combined organics are dried over Na2SO4, The solvent is removed in vacuo to give I-110 (360 mg, quantitative).
Workup
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c4f9b93c97774a58893ec34b132b60d2
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174980B2
Reaction notes
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