Dimethylformamide → HCID 59375121, compound

HRID 1811169Notes

Reaction equation

HRID 1811169 reaction equation
[Br:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([CH:15]([OH:18])[CH2:16][OH:17])=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:5]([C:19]([NH2:21])=[O:20])=[CH:4][CH:3]=1.O.[C:23]1(C)[CH:28]=CC(S(O)(=O)=O)=C[CH:24]=1.COC(OC)(C)C.CN(C=O)C>CCOC(C)=O>[Br:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([CH:15]4[CH2:16][O:17][C:23]([CH3:28])([CH3:24])[O:18]4)=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:5]([C:19]([NH2:21])=[O:20])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 64952,2-DimethoxypropaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 59375164HCID 59375164, compound

Product 1

HCID 59375121HCID 59375121, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-bromo-7-(1,2-dihydroxyethyl)-9H-carbazole-1-carboxamide (Example 68-1, 50 mg, 0.143 mmol) and p-toluenesulfonic acid monohydrate (8.2 mg, 0.043 mmol) in 2,2-dimethoxypropane (1.76 mL, 14.32 mmol) was stirred at rt. DMF (0.5 mL) was added and the mixture was stirred overnight. The mixture was diluted with EtOAc and washed with NaHCO3 (aq) and brine, then dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 75:25 to 50:50 hexane-EtOAc) to provide 4-bromo-7-(2,2-dimethyl-1,3-dioxolan-4-yl)-9H-carbazole-1-carboxamide as a light yellow solid (40 mg, 75% purity, 54%). Mass spectrum m/z 389, 391 (M+H)+.

Workup

  1. stirringthe mixture was stirred overnight
  2. washwashed with NaHCO3 (aq) and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (
  6. washeluting with a gradient from 75:25 to 50:50 hexane-EtOAc)

Sources & evidence

ORD record
ord-dc919b876bdc47c9ba3070383d0484b2
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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