N-bromobutanimide → HCID 22049892、化合物

HRID 1867077ノート

反応式

HRID 1867077 の反応式
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=2[CH3:23])[C:16]([O:18][CH3:19])=[O:17])[C:8](=[O:24])[CH:7]=1.[Br:30]N1C(=O)CCC1=O>C(Cl)Cl>[Br:30][C:7]1[C:8](=[O:24])[N:9]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=2[CH3:23])[C:16]([O:18][CH3:19])=[O:17])[C:10]([CH3:12])=[CH:11][C:6]=1[O:5][CH2:4][C:3]1[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:2]=1[F:1]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 22050431HCID 22050431、化合物

生成物 1

HCID 22049892HCID 22049892、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Methyl 3-[4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzoate (as prepared above) (1.8 g, 4.51 mmol) was taken up in CH2Cl2 (10 ml). N-bromosuccinimide (0.80 g, 4.51 mmol) was added and the mixture stirred at room temperature for two 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 (0.30 g, 14%, first crop) 1H NMR (300 MHz, CDCl3) δ 8.06 (dd, J=8.06, 1.61 Hz, 1H), 7.80 (d, J=1.61 Hz, 2H), 7.65 (app q, J=8.46 Hz, 1H), 7.48 (d, J=8.06, 1H), 7.05-6.99 (m, 1H), 6.96-6.89 (m, 1H), 6.16 (s, 1H), 5.31 (s, 2H), 3.93 (s, 3H), 2.17 (s, 3H), 1.96 (s, 3H). ES-HRMS m/z 478.0476 (M+H calcd for C22H19BrF2NO4 requires 478.0476).

後処理

  1. customThe CH2Cl2 is removed in vacuo
  2. customThe resulting precipitate is collected on a filter pad
  3. washwashed with CH3CN
  4. customto yield a white solid (0.30 g, 14%, first crop) 1H NMR (300 MHz, CDCl3) δ 8.06 (dd, J=8.06, 1.61 Hz, 1H), 7.80 (d, J=1.61 Hz, 2H), 7.65 (app q, J=8.46 Hz, 1H), 7.48 (d, J=8.06, 1H), 7.05-6.99 (m, 1H), 6.96-6.89 (m, 1H), 6.16 (s, 1H), 5.31 (s, 2H), 3.93 (s, 3H), 2.17 (s, 3H), 1.96 (s, 3H)

出典と根拠

ORDレコード
ord-6cf747975efd437c85700a0a9e4486a4
出典データセット
uspto-grants-2009_12
特許番号
US07629363B2

反応ノート

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