Acetic Acid → HCID 66604388, compound

HRID 2410663Notes

Reaction equation

HRID 2410663 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=3)=[C:11]([C:27]#[N:28])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(O)(=[O:31])C>C(O[Pd]OC(=O)C)(=O)C>[C:27]([C:11]1[CH:10]=[C:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH:14]=[C:13]2[C:12]=1[NH:15][C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][C:17]2=1)(=[O:31])[NH2:28]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 66604928HCID 66604928, compound

Product 1

HCID 66604388HCID 66604388, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

Ethyl 4-(3′,4′-dichloro-3-cyanobiphenyl-4-ylamino)benzoate (410 mg, 0.997 mmol), diacetoxypalladium (560 mg, 2.492 mmol) in glacial acetic acid (20 mL) in a microwave tube (20 mL) were heated in microwave reactors at 160° C. for 4 h. The reaction was cooled to room temperature. The catalyst was filtered off and solid was washed with acetic acid several times. The filtrate was concentrated under reduced pressure and the residue was co-evaporated with toluene (3×). The resulting residue was suspended in ethyl acetate. The solid was collected by filtration and air dried to afford 75.4 mg of ethyl 8-carbamoyl-6-(3,4-dichlorophenyl)-9H-carbazole-3-carboxylate. MS (ESI) m/z 425.1(M−H). 1H NMR (DMSO-d6) δ ppmH NMR (DMSO-d6) d ppm 11.87 (1H, s), 9.00 (2H, m), 8.41 (1H, br. s), 8.40 (1H, d, J=1.22 Hz), 8.30 (1H, d, J=2.14 Hz), 8.06 (1H, dd, J=8.55, 1.53 Hz), 8.01 (1H, dd, J=8.24, 2.14 Hz), 7.82 (1H, d, J=8.55 Hz), 7.78 (1H, d, J=8.55 Hz), 7.65 (1H, br. s.), 4.38 (2H, q, J=7.22 Hz), 1.39 (3H, t, J=7.17 Hz).

Workup

  1. filtrationThe catalyst was filtered off
  2. washsolid was washed with acetic acid several times
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. filtrationThe solid was collected by filtration and air
  5. customdried

Sources & evidence

ORD record
ord-9ce14251603d433088027c75977ba32b
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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