Methylamine → HCID 18385285, compound

HRID 2298242Notes

Reaction equation

HRID 2298242 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.Br[CH2:14][C:15]1[CH:16]=[C:17]([CH:30]=[CH:31][CH:32]=1)[CH2:18][N:19]1C(=O)C2C(=CC=CC=2)C1=O.CN>CN(C=O)C.C(OCC)(=O)C>[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:14][C:15]1[CH:16]=[C:17]([CH:30]=[CH:31][CH:32]=1)[CH2:18][NH2:19])[CH:8]=[CH:7]2

Participants

7

Reactant 4

HCID 6329MethylamineHCID 24758Sodium hydrideHCID 678615-FluoroindoleHCID 309016HCID 309016, compound

Product 1

HCID 18385285HCID 18385285, compoundYield 110.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydride (55% dispersion in oil, 63 mg, 1.44 mmol) was added to a solution of 5-fluoro-indol (150 mg, 1.11 mmol) in dry DMF (3 mL). The mixture was stirred under nitrogen for 15 min. 2-(3-Bromomethyl-benzyl)-isoindole-1,3-dione (403 mg, 1.22 mmol) was added and the mixture was stirred at room temperature over night. After cooling, aqueous methylamine (40%, 5 mL) was added and this mixture was heated at 80° C. over night. Ethyl acetate was added and the organic phase was washed three times with water, brine, dried and concentrated to give 312 mg of the sub-title compound sufficiently pure for the next step.

Workup

  1. stirringthe mixture was stirred at room temperature over night
  2. temperatureAfter cooling
  3. washthe organic phase was washed three times with water, brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6e38a33fefc04f6d9494f806127a45e4
Source dataset
uspto-grants-2002_12
Patent number
US06492406B1

Reaction notes

Loading…