N-bromobutanimide → HCID 22050037, compound

HRID 1867113Notes

Reaction equation

HRID 1867113 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N:12]1[C:17]([CH3:18])=[CH:16][C:15]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[F:28])=[CH:14][C:13]1=[O:29])[C:5]([O:7][CH3:8])=[O:6].[Br:30]N1C(=O)CCC1=O>C(Cl)Cl>[Br:30][C:14]1[C:13](=[O:29])[N:12]([C:11]2[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=2[Cl:1])[C:17]([CH3:18])=[CH:16][C:15]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[F:28]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22049965HCID 22049965, compound

Product 1

HCID 22050037HCID 22050037, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 3-chloro-4-[4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]benzoate (from step 2) (2.60 g, 6.21 mmol) was taken up in CH2Cl2 (20 ml). N-bromosuccinimide (1.11 g, 6.21 mmol) was added and the mixture stirred at room temperature for 4 hours. The CH2Cl2 is removed in vacuo and the residue is taken up in CH3CN. The resulting precipitate is collected on a filter pad and washed with CH3CN to yield a white solid (0.75 g, 24%). 1H NMR (300 MHz, CDCl3) δ 8.22 (d, J=1.88 Hz, 1H), 8.06 (dd, J=8.19, 1.75 Hz, 1H), 7.59 (app q, J=8.46 Hz, 1H), 7.33 (d, J=8.19, 1H), 6.96 (dt, J=8.06, 1.21 Hz, 1H), 6.89-6.84 (m, 1H), 6.13 (s, 1H), 5.26 (s, 2H), 3.95 (s, 3H), 1.95 (s, 3H); ES-MS m/z 478 (M+H). ES-HRMS m/z 497.9892 (M+H calcd for C22H16BrClF2NO4 requires 497.9914).

Workup

  1. customThe CH2Cl2 is removed in vacuo
  2. customThe resulting precipitate is collected on a filter pad
  3. washwashed with CH3CN

Sources & evidence

ORD record
ord-c8012d5e945b4b21a2eca459c70b6dba
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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