Dimethylamine → HCID 44465844, compound

HRID 241608Notes

Reaction equation

HRID 241608 reaction equation
Br[C:2]1[N:3]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[C:4]2[C:9]([C:10]=1[C:11]#[N:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:20][NH:21][CH3:22]>CN(C=O)C.O.C(Cl)Cl>[CH3:20][N:21]([CH3:22])[C:2]1[N:3]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[C:4]2[C:9]([C:10]=1[C:11]#[N:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 2

HCID 674DimethylamineHCID 44241532HCID 44241532, compound

Product 1

HCID 44465844HCID 44465844, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromo-1-(4-hydroxy-phenyl)-1H-indole-3-carbonitrile (Example 1) was mixed with excess dimethylamine in DMF (1:3) and the mixture was stirred in a sealed vial at 80° C. over night. The reaction-mixture was cooled to rt, diluted with H2O and DCM and then the phases were separated. The organic phase was evaporated to dryness and subjected to reversed phase preparative HPLC. Appropriate fractions were combined and evaporated, and identified by 1H-NMR and LC/MS. Purity was determined by analytical HPLC, ES/MS m/z: 278.1 (M+H), 276.1 (M−H); 1H NMR (acetone-d6, 500 MHz): 7.42 (m, 1H), 7.33 (m, 2H), 7.17 (m, 1H), 7.09-7.05 (m, 3H), 6.95 (m, 1H) and 2.93 (s, 6H).

Workup

  1. temperatureThe reaction-mixture was cooled to rt
  2. customthe phases were separated
  3. customThe organic phase was evaporated to dryness
  4. customevaporated

Sources & evidence

ORD record
ord-533ebd7fe2584c8aadb848dbbb68c363
Source dataset
uspto-grants-2014_02
Patent number
US08653072B2

Reaction notes

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