Benzyl Bromide → HCID 87105748, compound

HRID 1803766Notes

Reaction equation

HRID 1803766 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:11][CH:12]=2)[NH:7][CH2:6][CH2:5]1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>C(#N)C>[CH3:1][O:2][N:3]=[C:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([F:15])([F:17])[F:16])=[CH:11][CH:12]=2)[N:7]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 136359357HCID 136359357, compound

Product 1

HCID 87105748HCID 87105748, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of Example 16D (1.71 g, 7.0 mmol), benzyl bromide (0.88 mL, 7.35 mmol), diisopropylethylamine (2.44 mL, 14.0 mmol) in acetonitrile (12 mL) were heated in a microwave Personal Chemistry at 150° C. for 40 minutes. Ethyl acetate (200 mL) was added and the organic layer was washed twice with water (200 mL) and brine, dried over sodium sulfate, filtered, concentrate under reduced pressure, and chromatographed on silica gel eluting with 0-10% ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.84 (t, J=6.61 Hz, 2H), 3.39 (t, J=6.61 Hz, 2H), 3.93 (s, 3H), 4.60 (s, 2H), 6.90 (m, 2H), 7.31 (m, 5H), 7.90 (d, J=8.81 Hz, 1H). MS (DCI) m/z 335.10 (M+H)+.

Workup

  1. washthe organic layer was washed twice with water (200 mL) and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrate under reduced pressure
  5. customchromatographed on silica gel eluting with 0-10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-28b3888669e24ef4984ad65775a3a173
Source dataset
uspto-grants-2013_01
Patent number
US08350083B2

Reaction notes

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