Acetic Acid → HCID 66605267, compound

HRID 2410714Notes

Reaction equation

HRID 2410714 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([F:27])[CH:20]=2)[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:30])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][C:22]([O:25][CH3:26])=[C:21]([F:27])[CH:20]=2)[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:30])[NH2:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 66599408HCID 66599408, compound

Product 1

HCID 66605267HCID 66605267, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
130 °C

Procedure

A 350 ml pressure flask was loaded with 4-(3-cyano-3′-fluoro-4′-methoxybiphenyl-4-ylamino)benzoic acid (4.52 g, 9.73 mmol), acetic Acid (200 mL) and palladium(II) acetate (4.37 g, 19.46 mmol), sealed and heated to 130° C. for 12 hours. The mixture was filtered through CELITE®, the solids washed with acetic acid and the collected filtrate concentrated in vacuum. 2.14 g brown solid 8-carbamoyl-6-(3-fluoro-4-methoxyphenyl)-9H-carbazole-3-carboxylic acid were isolated and used without further purification. HPLC retention time 9.26 min (HPLC conditions as in Table 9 and Table 10). MS (ESI) m/z [M−H]− 477.

Workup

  1. customsealed
  2. filtrationThe mixture was filtered through CELITE®
  3. washthe solids washed with acetic acid
  4. concentrationthe collected filtrate concentrated in vacuum

Sources & evidence

ORD record
ord-3b798f34174a46baa4d75034aad81aff
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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