Diisopropylamine → 4-Fluoro-3-methyl-5-(tributylstannyl)pyridine

HRID 2069094ノート

反応式

HRID 2069094 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[CH3:20].[CH2:21]([Sn:25](Cl)([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH3:24].C(=O)(O)[O-].[Na+]>C1COCC1>[F:13][C:14]1[C:19]([Sn:25]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:21][CH2:22][CH2:23][CH3:24])=[CH:18][N:17]=[CH:16][C:15]=1[CH3:20]

参加物

7

反応物 5

HCID 7912DiisopropylamineHCID 15096Tributyltin ChlorideHCID 516892Sodium BicarbonateHCID 27629214-Fluoro-3-methylpyridineHCID 178418339Butyllithium

生成物 1

HCID 595351114-Fluoro-3-methyl-5-(tributylstannyl)pyridine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A THF (1 mL) solution of diisopropylamine (160 μL; WAKO) was cooled to −78° C. under a nitrogen atmosphere followed by the dropwise addition of normal butyllithium (2.6 M, 430 μL; KANTO). The resulting mixture was stirred as it was for 30 minutes followed by the dropwise addition of a THF (1 mL) solution of 4-fluoro-3-methylpyridine (111 mg) and the resulting mixture was further stirred for 1 hour. Then tri-n-butyltin chloride (330 μL; TCI) was added and the resulting mixture was slowly raised to room temperature and then stirred for 2 hours. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture solution, to the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine. The organic layer was dried and the solvent was evaporated under reduced pressure to give the title compound.

後処理

  1. stirringthe resulting mixture was further stirred for 1 hour
  2. stirringstirred for 2 hours
  3. extractionwas extracted with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. customThe organic layer was dried
  6. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-ec39fc47cccd4e13b10468c81d75859a
出典データセット
uspto-grants-2012_10
特許番号
US08299055B2

反応ノート

読み込み中…