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2,3-Dimethylbenzoic acid → Tert-butyl 4-(2,4-difluorophenyl)-2-(2,3-dimethylbenzamido)benzoate

HRID 1673445
Notes
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Reaction equation

HRID 1673445 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O.[NH2:18][C:19]1[CH:31]=[C:30]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=2[F:39])[CH:29]=[CH:28][C:20]=1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(=O)([O-])O.[Na+]>C(N(CC)CC)C.C(Cl)Cl.CN(C)C=O>[F:39][C:33]1[CH:34]=[C:35]([F:38])[CH:36]=[CH:37][C:32]=1[C:30]1[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:22])=[C:19]([NH:18][C:10](=[O:12])[C:9]2[CH:13]=[CH:14][CH:15]=[C:16]([CH3:17])[C:8]=2[CH3:7])[CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 117822,3-Dimethylbenzoic acidHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 67342694Tert-butyl 2-amino-4-(2,4-difluorophenyl)benzoate

Product 1

HCID 67343241Tert-butyl 4-(2,4-difluorophenyl)-2-(2,3-dimethylbenzamido)benzoate

Reagents, catalysts & solvents 3

HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent2×
HCID 8471TriethylamineSolvent

Procedure

1.7 mL of methylene chloride, 1.0 μL of N,N-dimethylformamide and 0.025 mL of oxalyl chloride were added to 41 mg of 2,3-dimethylbenzoic acid at room temperature sequentially and stirred at the same temperature for 1 hour. The reaction mixture was added to a mixed solution of 49 mg of tert-butyl 2-amino-4-(2,4-difluorophenyl)benzoate, 2.8 mL of methylene chloride and 0.36 mL of triethylamine and stirred at room temperature for 1 hour. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the organic layer was separated, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate=4:1]to obtain tert-butyl 4-(2,4-difluorophenyl)-2-(2,3-dimethylbenzamido)benzoate.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. customthe organic layer was separated
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008

Sources & evidence

ORD record
ord-a0c5cdcc143d42efad12365784265f6c
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07999132B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes