Sodium Carbonate → HCID 87071493, compound

HRID 1811134Notes

Reaction equation

[Br:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([CH:15]=O)=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:5]([C:17]([NH2:19])=[O:18])=[CH:4][CH:3]=1.Cl.[NH2:21][OH:22].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Br:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10](/[CH:15]=[N:21]/[OH:22])=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:5]([C:17]([NH2:19])=[O:18])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

Step 1 A mixture of 4-bromo-7-formyl-9H-carbazole-1-carboxamide (prepared according to Step 1 of Example 41-1, 200 mg, 0.631 mmol) and hydroxylamine hydrochloric acid salt (65.7 mg, 0.946 mmol) in ethanol (3 mL) was treated with 2 M aqueous sodium carbonate (0.236 mL, 0.473 mmol) and heated at 80-90° C. After 17.5 h, the mixture was cooled to rt and partitioned between EtOAc and water. The organic phase was dried and concentrated, and the residue was triturated with methanol, and the precipitate was collected by filtration, rinsed with methanol and dried to provide (E)-4-bromo-7-((hydroxyimino)methyl)-9H-carbazole-1-carboxamide as a gray-tan solid (110 mg, 53%). 1H NMR (400 MHz, DMSO-d6) δ 11.87 (1 H, s), 11.33 (1 H, s), 8.65 (1 H, d, J=8.4 Hz), 8.32 (1 H, s), 8.28 (1 H, br. s.), 8.09 (1 H, s), 7.92 (1 H, d, J=8.1 Hz), 7.64 (1 H, br. s.), 7.58 (1 H, d, J=8.6 Hz), 7.51 (1 H, d, J=8.1 Hz). Mass spectrum m/z 332, 334 (M+H)+.

Workup

temperaturethe mixture was cooled to rt
custompartitioned between EtOAc and water
customThe organic phase was dried
concentrationconcentrated
customthe residue was triturated with methanol
filtrationthe precipitate was collected by filtration
washrinsed with methanol
customdried

Sources & evidence

ORD record: ord-daa90cc02a3d47b78a0de12b9c95ab64
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362065B2

Reaction notes

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