N-bromobutanimide → HCID 22050887, compound

HRID 1867066Notes

Reaction equation

HRID 1867066 reaction equation
[F:1][C:2]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]([C:13]2[CH:18]=[C:17]([CH2:19][OH:20])[CH:16]=[CH:15][C:14]=2[CH3:21])[C:8](=[O:22])[CH:7]=1.[Br:28]N1C(=O)CCC1=O>C(Cl)Cl>[Br:28][C:7]1[C:8](=[O:22])[N:9]([C:13]2[CH:18]=[C:17]([CH2:19][OH:20])[CH:16]=[CH:15][C:14]=2[CH3:21])[C:10]([CH3:12])=[CH:11][C:6]=1[O:5][CH2:4][C:3]1[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22050979HCID 22050979, compound

Product 1

HCID 22050887HCID 22050887, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[(2,4-difluorobenzyl)oxy]-1-[5-(hydroxymethyl)-2-methylphenyl]-6-methyl-pyridin-2(1H)-one (from Step 2) (4.0 g, 10.8 mmol) was stirred at room temperature with N-bromosuccinimide (2.1 g, 11.9 mmol) in 100 ml of CH2Cl2 for 2.0 hours. The reaction was evaporated on a rotary evaporator and the resulting solid was washed with acetonitrile and dried in vacuo to yield a white solid (3.9 g, 80%). 1H NMR (300 MHz, CDCl3) δ 7.67 (app q, J=6.24 Hz, 1H), 7.35 (d, J=1.01 Hz, 2H), 7.10 (s, 1H), 7.04 (m, 1H), 6.91 (ddd, J=11.08, 8.66, 2.42 Hz, 1H), 6.15 (d, J=0.63 Hz, 2H), 5.29 (s, 2H), 4.66 (s, 2H), 2.08 (s, 3H), 1.97 (s, 3H); ES-MS m/z 450 (M+H). ES-HRMS m/z 450.0467 (M+H calcd for C21H19BrF2NO3 requires 450.0511).

Workup

  1. customThe reaction was evaporated on a rotary evaporator
  2. washthe resulting solid was washed with acetonitrile
  3. customdried in vacuo

Sources & evidence

ORD record
ord-e30db71689084a07b8ed99a4516bc045
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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