Acetic Acid → HCID 66599388, compound

HRID 2410708Notes

Reaction equation

HRID 2410708 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1)#[N:2].C(O)(=[O:29])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[CH:6]=[C:7]2[C:8]=1[NH:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[CH:17][C:18]2=1)(=[O:29])[NH2:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 66599405HCID 66599405, compound

Product 1

HCID 66599388HCID 66599388, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
130 °C

Procedure

A 5 ml microwave vial was loaded with 4-(3-cyano-2′-methoxybiphenyl-4-ylamino)benzoic acid (63 mg, 0.161 mmol), Acetic Acid (4 ml) and Palladium(II) acetate (106 mg, 0.472 mmol), sealed and heated to 130° C. for 12 hours. The reaction mixture was filtered through a 0.45 um Nylon filter, the filter rinsed with acetic acid and the collected liquids evaporated. 31.5 mg of 8-carbamoyl-6-(2-methoxyphenyl)-9H-carbazole-3-carboxylic acid were isolated as a brown film and used without further purification. MS (ESI) m/z 359 (M−H).

Workup

  1. customsealed
  2. filtrationThe reaction mixture was filtered through a 0.45 um Nylon
  3. filtrationfilter
  4. washthe filter rinsed with acetic acid
  5. customthe collected liquids evaporated

Sources & evidence

ORD record
ord-f938f53252a04486a32b37be9e3b2f63
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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