N-Bromosuccinamide → HCID 22051023, compound

HRID 1832047Notes

Reaction equation

HRID 1832047 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]=[CH:17][C:16]([CH:19]=[CH2:20])=[CH:15][C:14]=2[CH3:21])[C:8](=[O:22])[CH:7]=1.[Br:28]NC(=O)CCC(N)=O>C(#N)C>[Br:28][C:7]1[C:8](=[O:22])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]=[CH2:20])=[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 9834204N-BromosuccinamideHCID 22050300HCID 22050300, compound

Product 1

HCID 22051023HCID 22051023, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared by reacting 4-[(2,4-difluorobenzyl)oxy]-6-methyl-1-(2-methyl-4-vinylphenyl)pyridin-2(1H)-one (0.64 g, 1.74 mmol) with N-bromosuccinamide (0.325 g, 1.83 mmol) in acetonitrile (9 mL) at 0° C. using a similar procedure as described in step 3 of Example 465, to give 0.423 g (54.5% after recrystallization) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 7.67 (app q, J=7.59 Hz, 1H), 7.48 (s, 1H), 7.42 (dd, J=8.21, 1.98 Hz, 1H), 7.33 (dt, J=10.00, 2.27 Hz, 1H), 7.17 (dt, J=8.51, 2.44 Hz, 1H), 7.13 (d, J=7.88 Hz, 1H), 6.74 (dd, J=11.29, 6.34 Hz, 1H), 6.67 (s, 1H), 5.88 (d, J=17.85, 1H), 5.32-5.30 (m, 2H), 1.92 (s, 3H), 1.88 (s, 3H). ES-HRMS m/z 446.0579 (M+H calcd for C22H19BrF2NO2, requires 446.0568).

Workup

  1. customat 0° C.
  2. customto give
  3. custom0.423 g (54.5% after recrystallization) of the desired product

Sources & evidence

ORD record
ord-b973f390150d494ca140c53173650d11
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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