Methanol → 6-(Dimethylamino)pyridine-3-boronic acid

HRID 57528

反応式

HRID 57528 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH3:10])[CH3:9])=[N:6][CH:7]=1.[Li]CCCC.[B:16](OC(C)C)([O:21]C(C)C)[O:17]C(C)C.CO>C1COCC1>[CH3:9][N:8]([CH3:10])[C:5]1[N:6]=[CH:7][C:2]([B:16]([OH:21])[OH:17])=[CH:3][CH:4]=1

参加物

6

反応物 4

HCID 887MethanolHCID 21531Triisopropyl borateHCID 38030415-bromo-N,N-dimethylpyridin-2-amineHCID 178418339Butyllithium

生成物 1

HCID 27632716-(Dimethylamino)pyridine-3-boronic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-72 °C

実験手順

A solution of 5-bromo-N,N-dimethylpyridin-2-amine (500 mg, 2.5 mmol) in THF (10 mL) was treated with n-BuLi (1.2 mL, 3 mmol) at −72° C. for 2 hours. Triisopropyl borate (705 mg, 3.75 mmol) was then added dropwise. After the completion of the addition, the mixture was stirred at −72° C. for an additional 1 hour and slowly warmed up and stirred at the ambient temperature overnight. MeOH was carefully added, and the volatiles were removed under reduced pressure to give the title compound. MS (m/z): 167 (M+H)+.

後処理

  1. additionAfter the completion of the addition
  2. temperatureslowly warmed up
  3. stirringstirred at the ambient temperature overnight
  4. customthe volatiles were removed under reduced pressure

出典と根拠

ORDレコード
ord-1d1e0032d13f4159b2fc306ea574db4d
出典データセット
uspto-grants-2016_09
特許番号
US09434726B2

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