HCID 59198417, compound → HCID 59198468, compound

HRID 1896511Notes

Reaction equation

HRID 1896511 reaction equation
Br[C:2]1[C:7]2[NH:8][C:9]3[CH:10]=[CH:11][C:12]([F:15])=[CH:13][C:14]=3[C:6]=2[C:5]([NH:16][CH3:17])=[N:4][CH:3]=1.[Cu][C:19]#[N:20]>CN1C(=O)CCC1.C(OCC)(=O)C>[F:15][C:12]1[CH:11]=[CH:10][C:9]2[NH:8][C:7]3[C:2]([C:19]#[N:20])=[CH:3][N:4]=[C:5]([NH:16][CH3:17])[C:6]=3[C:14]=2[CH:13]=1

Participants

5

Reactant 2

HCID 59198417HCID 59198417, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 59198468HCID 59198468, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
225 °C

Procedure

4-Bromo-8-fluoro-N-methyl-5H-pyrido[4,3-b]indol-1-amine (150 mg, 0.501 mmol) was combined with copper(I) cyanide (114 mg, 1.275 mmol) and dissolved in NMP (2.55 mL). The reaction was heated to 225° C. in a microwave for one hr. The solution was cooled to ambient temperature, diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated. The crude residue was purified on silica gel (EtOAc/hexanes).

Workup

  1. temperatureThe solution was cooled to ambient temperature
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified on silica gel (EtOAc/hexanes)

Sources & evidence

ORD record
ord-119b0e54374d4894a10a0c3959c60dbe
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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