Water → HCID 67975063, compound

HRID 468838Notes

Reaction equation

HRID 468838 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:19])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH2:18])[N:14]=[CH:15]3)=[CH:10][CH:9]=2)[CH:7]=1.[Br:20]N1C(=O)CCC1=O.O.C(=O)(O)[O-].[Na+]>CO>[Br:20][C:12]1[C:11]2[C:16](=[CH:17][C:8]([C:6]3[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[CH3:19])=[CH:9][CH:10]=2)[CH:15]=[N:14][C:13]=1[NH2:18]

Participants

6

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 574102447-(5-Fluoro-2-methylphenyl)isoquinolin-3-amine

Product 1

HCID 67975063HCID 67975063, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-(5-Fluoro-2-methylphenyl)isoquinolin-3-amine (51.3 mg, 203 μmol) and N-bromosuccinimide (36.4 mg, 204 μmol) were dissolved together in methanol (2.0 mL) at ambient temperature. After 10 mins the mixture was poured into water and saturated aqueous sodium bicarbonate (1 mL), extracted twice into dichloromethane. The combined organic phases were washed with brine containing sodium thiosulfate (1 mL, 1M), dried over sodium sulfate, filtered and concentrated in vacuo to afford a residue that was purified by flash chromatography (silica, ISCO, 0-10% methanol in dichloromethane) to yield the title compound as a white solid (46.3 mg, 69%). 1H NMR (400 MHz, CDCl3) δ 8.79 (s, 1H), 7.92 (t, J=9 Hz, 1H), 7.71 (s, 1H), 7.59 (d, J=9 Hz, 1H), 7.27-7.22 (m, 1H), 7.03-6.95 (m, 2H), 5.04 (s, 2H), 2.24 (s, 3H). LCMS: M+H+=331 & 333.

Workup

  1. extractionextracted twice into dichloromethane
  2. washThe combined organic phases were washed with brine
  3. additioncontaining sodium thiosulfate (1 mL, 1M)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a residue that
  8. customwas purified by flash chromatography (silica, ISCO, 0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-fab32790ad834ea2b81019392464d754
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

Loading…