N-Bromosuccinamide → HCID 22050601, compound

HRID 1832049Notes

Reaction equation

HRID 1832049 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([N:11]2[C:16]([CH3:17])=[CH:15][C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[F:27])=[CH:13][C:12]2=[O:28])[CH:5]=1.[Br:30]NC(=O)CCC(N)=O>C(#N)C>[Br:30][C:13]1[C:12](=[O:28])[N:11]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=2[Cl:10])[C:3]([O:2][CH3:1])=[O:29])[C:16]([CH3:17])=[CH:15][C:14]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[F:27]

Participants

4

Reactant 2

HCID 9834204N-BromosuccinamideHCID 22050976HCID 22050976, compound

Product 1

HCID 22050601HCID 22050601, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

methyl 3-[3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-chlorobenzoate was prepared by reacting methyl-4-chloro-3-[4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]benzoate (2.3 g, 5.47 mmol) with N-bromosuccinamide (0.97 g, 5.47 mmol) in acetonitrile (10 mL) at 0° C., using a similar procedure as described in step 3 of Example 465, to give 1.80 g (66.2%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 8.06-8.03 (m, 2H), 7.86 (d, J=9.70 Hz, 1H), 7.68 (q, J=7.62, 1H), 7.34 (dt, J=10.07, 2.46 Hz, 1H), 7.17 (dt,J=8.72, 2.90 Hz, 1H), 6.73 (s, 1H), 5.33 (s, 2H), 3.85 (s, 3H), 1.91 (s, 3H). ES-MS m/z 495.9757 (M−H calcd for C21H14BrClF2NO4, requires 495.9795).

Workup

  1. custommethyl 3-[3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-chlorobenzoate was prepared
  2. customat 0° C.

Sources & evidence

ORD record
ord-77fe96be787946459bd0b99c3528aaa5
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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