Potassium Carbonate → HCID 59375045, compound

HRID 661949Notes

Reaction equation

HRID 661949 reaction equation
[OH:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([N:24]5[CH2:32][C:31]6[C:26](=[CH:27][C:28]([CH3:33])=[CH:29][CH:30]=6)[C:25]5=[O:34])[C:19]=4[CH3:35])=[CH:8][CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:43][CH2:44][O:45][CH3:46]>CN(C=O)C>[CH3:46][O:45][CH2:44][CH2:43][O:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([N:24]5[CH2:32][C:31]6[C:26](=[CH:27][C:28]([CH3:33])=[CH:29][CH:30]=6)[C:25]5=[O:34])[C:19]=4[CH3:35])=[CH:8][CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 66606478HCID 66606478, compound

Product 1

HCID 59375045HCID 59375045, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-hydroxy-4-(2-methyl-3-(6-methyl-1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide (Example 40-2, 30 mg, 0.065 mmol) and potassium carbonate (18 mg, 0.130 mmol) in DMF (1.0 mL) was stirred at rt for 30 min, then was treated with 1-bromo-2-methoxyethane (14 mg, 0.098 mmol). The mixture was heated at 90° C. for 4 h, cooled to rt and concentrated under vacuum. The residue was purified by preparative HPLC to provide 7-(2-methoxyethoxy)-4-(2-methyl-3-(6-methyl-1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide as a white solid (12.5 mg, 35%). 1H NMR (400 MHz, DMSO-d6) δ 11.39 (1H, s), 8.17 (1 H, br. s.), 7.95 (1H, d, J=7.9 Hz), 7.54-7.64 (3H, m), 7.49 (3H, t, J=8.0 Hz), 7.27-7.38 (2H, m), 7.00 (1H, d, J=7.9 Hz), 6.91 (1H, d, J=8.8 Hz), 6.59 (1H, dd, J=8.8, 2.4 Hz), 4.91 (2H, d, J=3.3 Hz), 4.12 (2H, dd, J=5.5, 3.1 Hz), 3.63-3.75 (2H, m), 3.33 (3H, s), 2.44 (3H, s), 1.83 (3H, s). Mass spectrum m/z 520.1 (M+H)+.

Workup

  1. temperatureThe mixture was heated at 90° C. for 4 h
  2. temperaturecooled to rt
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-ab03c9aa7dae4ee8bdfa4eb82bdbd321
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

Loading…