Dimethylformamide → HCID 86600272, compound

HRID 916949Notes

Reaction equation

HRID 916949 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[F:34])[CH2:5][O:6][C:7]1[C:12]([C:13]([OH:15])=O)=[CH:11][C:10]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[C:9]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])[N:8]=1.CN(C=O)C.C(Cl)(=O)C([Cl:43])=O>C(Cl)Cl>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:10]2[C:9]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[Cl:30])=[N:8][C:7]([O:6][CH2:5][C:4]3[CH:31]=[CH:32][C:33]([F:34])=[C:2]([F:1])[CH:3]=3)=[C:12]([CH:11]=2)[C:13]([Cl:43])=[O:15])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 10152588HCID 10152588, compound

Product 1

HCID 86600272HCID 86600272, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3,4-difluorobenzyloxy)-6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carboxylic acid (120 mg, 0.20 mmol) from Example 77 in methylene chloride (3 mL) was added a drop of DMF (cat.) and oxalyl chloride (0.100 mL, 1.1 mmol). The reaction was stirred at rt for 1 h and was then evaporated to dryness. The acid chloride was dissolved in methylene chloride and used directly in the subsequent amide formation.

Workup

  1. customwas then evaporated to dryness
  2. dissolutionThe acid chloride was dissolved in methylene chloride

Sources & evidence

ORD record
ord-1464e2a1e121441383cc36544ec317f1
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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