Dimethylformamide → HCID 59375121, compound

HRID 661989Notes

Reaction equation

HRID 661989 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-75e4e5831cd744c09ce8c4cdc3f61ca3
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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