Acetic Acid → HCID 66603955, compound

HRID 2410698Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=2)[CH:6]=[CH:7][C:8]=1[NH:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14])#[N:2].CC(O)=[O:30]>C(O[Pd]OC(=O)C)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=2)[CH:6]=[C:7]2[C:8]=1[NH:9][C:10]1[CH:11]=[C:12]([C:13]([O:15][CH3:16])=[O:14])[CH:17]=[CH:18][C:19]2=1)(=[O:30])[NH2:2]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of methyl 3-(3-cyano-3′-methoxybiphenyl-4-ylamino)benzoate (3.3 g, 9.21 mmol), diacetoxypalladium (5.17 g, 23.02 mmol), and AcOH (150 mL) in a pressure vessel was heated at 130° C. for 48 h. The sold was separated by filtration and washed with several times with HOAc. The filtrate was taken and the HOAc was removed under reduced pressure. The residue was dissolved in a mixture of DCM and MeOH and mixed with silica gel (12 g). After the removal of solvents, the mixture was loaded to a silica gel column and eluted with DCM containing 0 to 1.5% MeOH to afford 140 mg of methyl 8-carbamoyl-6-(3-methoxyphenyl)-9H-carbazole-2-carboxylate. MS (ESI) m/z 375.2 (M+H). 1H NMR (MeOD) δ ppm 9.28 (1H, d, J=1.53 Hz), 8.18 (1H, d, J=1.53 Hz), 7.86 (1H, d, J=7.32 Hz), 7.78 (1H, d, J=7.93 Hz), 7.46 (1H, t, J=7.78 Hz), 7.32-7.41 (2H, m), 7.31 (1H, d, J=2.14 Hz), 6.88 (1H, dd, J=7.48, 1.98 Hz), 4.04 (3H, s), 3.89 (3H, s).

Workup

customThe sold was separated by filtration
washwashed with several times with HOAc
customthe HOAc was removed under reduced pressure
dissolutionThe residue was dissolved in a mixture of DCM and MeOH
additionmixed with silica gel (12 g)
customAfter the removal of solvents
washeluted with DCM containing 0 to 1.5% MeOH

Sources & evidence

ORD record: ord-875b9f598cc2422c8f95408bd9d2bb36
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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