Diethyl Ether → HCID 67220629, compound

HRID 1962395Notes

Reaction equation

HRID 1962395 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[C:8]([CH3:19])=[CH:7]2.[Br:20]N1C(=O)CCC1=O.C(OCC)C.C(OCC)(=O)C>CN(C)C=O>[Br:20][C:8]1([CH3:19])[CH2:7][C:6]2[C:11](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=2)[C:10](=[O:12])[N:9]1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 58286923HCID 58286923, compound

Product 1

HCID 67220629HCID 67220629, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

8-Fluoro-3-methyl-2-pyridin-3-yl-2H-isoquinolin-1-one (550 mg, 2.2 mmol) and N-bromosuccinimide (396 mg, 2.23 mmol) were dissolved in N,N-dimethylformamide (10 mL). The reaction mixture was stirred at 50° C. for 60 minutes and poured into diethyl ether (50 mL) and ethyl acetate (20 mL). A white solid precipitated, which was removed by filtration. The filtrate was washed with diluted brine (water/sat. NaCl (aq.)=1:1; 4×20 mL), dried over MgSO4 and rotavaped. 1H NMR (500 MHz, CDCl3): 2.27 (s, 3H, Me), 7.2 (dd, J=8.4 Hz, J=10.7 Hz, 1H), 7.52 (dd, J=4.9 Hz, J=7.9 Hz, 1H), 7.64 (d (d of unresolved m), J=8 Hz, 1H), 7.72 (td, J(d)=5 Hz, J(t)=8.1 Hz, 1H), 7.84 (d, J=8.2 Hz), 8.53 (d, J=1.8 Hz, 1H), 8.74 (d, J=4.3 Hz, 1H).

Workup

  1. customA white solid precipitated
  2. customwhich was removed by filtration
  3. washThe filtrate was washed with diluted brine (water/sat. NaCl (aq.)=1:1; 4×20 mL)
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-7fc611ee2ffd4db5a0d191a70fddb1da
Source dataset
uspto-grants-2013_04
Patent number
US08415356B2

Reaction notes

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