Triethylamine → HCID 117771406、化合物

HRID 2201526ノート

反応式

HRID 2201526 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.[Br:10][C:11]1[N:16]=[C:15]([C:17](O)=[O:18])[C:14]([O:20][CH3:21])=[CH:13][CH:12]=1.C(N(CC)CC)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(Cl)Cl.O>[Br:10][C:11]1[N:16]=[C:15]([C:17]([NH:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:18])[C:14]([O:20][CH3:21])=[CH:13][CH:12]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 660364-ChlorobenzylamineHCID 111923Propylphosphonic anhydrideHCID 714639656-Bromo-3-methoxypicolinic acid

生成物 1

HCID 117771406HCID 117771406、化合物収率 87%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of (4-chlorophenyl)methanamine (610 mg, 4.31 mmol), 6-bromo-3-methoxypicolinic acid (1.0 g, 4.31 mmol) and triethylamine (1.31 g, 12.9 mmol) in DCM (10 mL) was added dropwise T3P (2.74 g, 8.61 mmol) at 0° C. Five minutes later, TLC indicated the reaction was complete, and the mixture was suspended in water and extracted with DCM. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo to give the crude 6-bromo-N-(4-chlorobenzyl)-3-methoxypicolinamide (1.3 g, yield: 87%) without further purification. 1H-NMR (DMSO-d6, 400 MHz) δ 8.98 (t, J=6.0 Hz, 1H), 7.69 (d, J=8.8 Hz, 1H), 7.58 (d, J=8.8 Hz, 1H), 7.39˜7.43 (m, 2H), 7.33 (d, J=8.4 Hz, 2H), 4.22 (d, J=6.4 Hz, 2H), 3.84 (s, 3H). MS (M+H)+: 355/357.

後処理

  1. customFive minutes
  2. extractionextracted with DCM
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-05e6393fd5374acc85faaf7786881df4
出典データセット
uspto-grants-2016_06
特許番号
US09364482B2

反応ノート

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