Carbon Dioxide → HCID 46935552, compound

HRID 1626728Notes

Reaction equation

HRID 1626728 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=[CH:15][CH:16]=2)=[O:10])=[C:4](I)[CH:3]=1.[C:24](=[O:26])=[O:25]>C1COCC1.C(OCC)(=O)C>[C:13]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=[C:11]([C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[C:24]([OH:26])=[O:25])=[O:10])[CH:12]=1

Participants

5

Reactant 2

HCID 280Carbon DioxideHCID 66679859HCID 66679859, compound

Product 1

HCID 46935552HCID 46935552, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

433 mg (1.0 mmol) of N-(4-chloro-2-iodophenyl)biphenyl-3-carboxamide was dissolved in 5 mL of THF solution, and 1.6M n-butyllithium(n-BuLi)hexane solution (1.25 mL) was added dropwise under an Ar atmosphere at −78° C. The mixture was stirred for 0.5 hours. Dry ice was added thereto, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with 1N hydrochloric acid and saturated saline, and dried over anhydrous sodium sulfate. The resultant was separated and purified by silica gel column chromatography, thereby giving 48.2 mg of the target 2-[(biphenyl-3-ylcarbonyl)amino]-5-chlorobenzoic acid (yield: 14%).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. washwashed with 1N hydrochloric acid and saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe resultant was separated
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-979cd7eb6f254359b0e935a26a40b3a0
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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