Diethyl Ether → HCID 58525647, compound

HRID 1962415Notes

Reaction equation

HRID 1962415 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]([CH2:13][C:14]1[O:15][CH:16]=[CH:17][N: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:7]1[C:6]2[C:11](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=2)[C:10](=[O:12])[N:9]([CH2:13][C:14]2[O:15][CH:16]=[CH:17][N:18]=2)[C:8]=1[CH3:19]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 58525657HCID 58525657, compound

Product 1

HCID 58525647HCID 58525647, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 8-fluoro-3-methyl-2-oxazol-2-ylmethyl-2H-isoquinolin-1-one (271 mg, 1.05 mmol) and N-bromosuccinimide (192 mg, 1.08 mmol) in N,N-dimethylformamide (4.8 mL) was stirred at 50° C. for 60 minutes. The reaction mixture was 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 evaporated to give a 321 mg of a solid (yield 90%), which was used in the next step without further purification. LC-MS (m/z) 337.3&339.4 (MH+), tR=1.1. 1H NMR (CDCl3, 500 MHz, TMS=0 ppm): 2.75 (s, 3H, Me), 5.52 (s, 2H, CH2), 7.07 (s (unres. d, J<1 Hz), 1H, oxazol), 7.16 (dd, J=8.1 Hz, J=11.1 Hz, 1H, C7-H), 7.62 (s (unres. d, J<1 Hz), 1H, oxazole), 7.66 (dt, J(t)=8.1 Hz, J(HF)=4.9 Hz, 1H, C6-H), 7.78 (d, J=8.2 Hz, 1H, C5-H).

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
  5. customevaporated

Sources & evidence

ORD record
ord-9ade5fe14eb540119fca67f83fe06245
Source dataset
uspto-grants-2013_04
Patent number
US08415373B2

Reaction notes

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