Dimethylformamide → HCID 59426440, compound

HRID 907141Notes

Reaction equation

HRID 907141 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[N:17]([CH2:29][CH3:30])[C:18]3[C:23]([C:24]=2[C:25]#[N:26])=[CH:22][CH:21]=[C:20]([O:27][CH3:28])[CH:19]=3)=[CH:10][CH:9]=1)=[O:6].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>CCOC(C)=O>[CH2:29]([N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[C:20]([O:27][CH3:28])[CH:19]=2)[C:24]([C:25]#[N:26])=[C:16]1[C:15]#[C:14][C:11]1[CH:12]=[CH:13][C:8]([N:7]2[CH2:2][CH2:3][NH:4][C:5]2=[O:6])=[CH:9][CH:10]=1)[CH3:30]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 59425711HCID 59425711, compound

Product 1

HCID 59426440HCID 59426440, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-(2-Chloroethyl)-3-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-ylethynyl)-phenyl] urea (55 mg, 0.13 mmol), prepared as in Example 1AC, was combined with K2CO3 (50 mg, 0.36 mmol) and DMF (550 μL). This mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted in EtOAc, and was washed with H2O, and then with brine. The organic layer was dried and concentrated. Purification by silica chromatography (10-50%, EtOAc/CH2Cl2) yielded 1-ethyl-6-methoxy-2-[4-(2-oxo-imidazolidin-1-yl)-phenylethynyl]-1H-indole-3-carbonitrile (47 mg, 94%) as a white solid.

Workup

  1. washwas washed with H2O
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customPurification by silica chromatography (10-50%, EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-7d7d33974e3e42c5a18f6d7384268807
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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