N-bromobutanimide → Methyl 4-(2-amino-5-bromopyridin-3-yl)-2-methylbenzoate

HRID 596081ノート

反応式

HRID 596081 の反応式
[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([CH3:18])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C1C(=O)N([Br:26])C(=O)C1>C(#N)C>[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([CH3:18])[CH:9]=2)=[CH:6][C:5]([Br:26])=[CH:4][N:3]=1

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 118046459Methyl 4-(2-aminopyridin-3-yl)-2-methylbenzoate

生成物 1

HCID 118045889Methyl 4-(2-amino-5-bromopyridin-3-yl)-2-methylbenzoate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

To a solution of methyl 4-(2-aminopyridin-3-yl)-2-methylbenzoate (4.2 g, 17.34 mmol) in acetonitrile (173 mL) was added NBS (3.15 g, 17.68 mmol) in two portions at 0° C. The reaction mixture was stirred at 0° C. for 20 min. LCMS showed the reaction completed. After quenched with sat. Na2SO3 and NaHCO3, the reaction mixture was stirred for 30 min. The reaction mixture was extracted with EtOAc 3 times, washed by sat NaHCO3, water and brine. The organics was dried over Na2SO4, filtered and concentrated. The crude material was triturated with ether and taken to the next step without further purification. LCMS (m/z): 323.1 (MH+), 0.68 min.

後処理

  1. customAfter quenched with sat. Na2SO3 and NaHCO3
  2. stirringthe reaction mixture was stirred for 30 min
  3. extractionThe reaction mixture was extracted with EtOAc 3 times
  4. washwashed
  5. dry with materialThe organics was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was triturated with ether
  9. customtaken to the next step without further purification
  10. custom323.1 (MH+), 0.68 min.

出典と根拠

ORDレコード
ord-4829d1540229494ab22631d82ec9770f
出典データセット
uspto-grants-2016_01
特許番号
US09242996B2

反応ノート

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