Potassium Carbonate → HCID 59375132, compound

HRID 661951Notes

Reaction equation

HRID 661951 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:36](=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH2:53][CH:54]2[O:58][C:57]([CH3:60])(C)[CH2:56][O:55]2)(=O)=O)=CC=1>CN(C=O)C.O>[CH3:36][C:54]1([CH3:53])[O:58][CH:57]([CH2:60][O:1][C:2]2[CH:14]=[C:13]3[C:5]([C:6]4[C:7]([C:18]5[CH:23]=[CH:22][CH:21]=[C:20]([N:24]6[CH2:32][C:31]7[C:26](=[CH:27][C:28]([CH3:33])=[CH:29][CH:30]=7)[C:25]6=[O:34])[C:19]=5[CH3:35])=[CH:8][CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]=4[NH:12]3)=[CH:4][CH:3]=2)[CH2:56][O:55]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66606478HCID 66606478, compoundHCID 87071561HCID 87071561, compound

Product 1

HCID 59375132HCID 59375132, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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, 50 mg, 0.108 mmol) and potassium carbonate (30 mg, 0.217 mmol) in DMF (1.7 mL) was stirred at rt for 30 min, then was treated with racemic (4,4-dimethyl-1,3-dioxolan-2-yl)methyl 4-methylbenzenesulfonate (46.5 mg, 0.163 mmol). The resulting mixture was heated at 80° C. overnight. The mixture was cooled to rt, diluted with water and extracted with EtOAc. The organic phase was washed with brine, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 50:50 to 80:20 EtOAc-hexane) to provide racemic 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-4-(2-methyl-3-(6-methyl-1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide as a light yellow solid (30 mg, 48%). Mass spectrum m/z 576.1 (M+H)+.

Workup

  1. temperatureThe resulting mixture was heated at 80° C. overnight
  2. temperatureThe mixture was cooled to rt
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (
  8. washeluting with a gradient from 50:50 to 80:20 EtOAc-hexane)

Sources & evidence

ORD record
ord-8443809ce64146dfa06a4b9bd86a42da
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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