N-methyl-2-pyrrolidone → 2-((Tert-butyldimethylsilyloxy)methyl)isonicotinonitrile

HRID 1807624ノート

反応式

HRID 1807624 の反応式
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH:3]=1.[CH3:17][N:18]1C(=O)CCC1>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Si:10]([O:9][CH2:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][N:5]=1)[C:17]#[N:18])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

参加物

5

反応物 2

HCID 13387N-methyl-2-pyrrolidoneHCID 583550294-Bromo-2-(((tert-butyldimethylsilyl)oxy)methyl)pyridine

生成物 1

HCID 583550752-((Tert-butyldimethylsilyloxy)methyl)isonicotinonitrile収率 26%

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
95 °C

実験手順

To a stirring solution of 4-bromo-2-((tert-butyldimethylsilyloxy)methyl)pyridine INT-70 (0.800 g, 2.6 mmol) in 3 mL of 1-methyl-2-pyrrolidine (NMP) was added zinc cyanide (0.610 g, 5.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.060 g, 0.052 mmol). The solution was degassed with N2 and the reaction mixture heated at 95° C. for 12 h. Upon cooling, the reaction mixture was diluted with saturated NaHCO3 and extracted with DCM. The combined organic layers were dried over MgSO4, filtered, and concentrated. The crude product was purified by chromatography (MeOH/DCM) to produce 0.170 g (26%) of 2-((tert-butyldimethylsilyloxy)methyl)isonicotinonitrile INT-71 as a light yellow solid. LCMS-ESI (m/z) calculated for C13H20N2OSi: 248.4; found 249.1 [M+H]+, tR=4.21 min (Method 1).

後処理

  1. customThe solution was degassed with N2
  2. temperatureUpon cooling
  3. additionthe reaction mixture was diluted with saturated NaHCO3
  4. extractionextracted with DCM
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography (MeOH/DCM)

出典と根拠

ORDレコード
ord-c3601b248be346f880fa55ccdda36d8d
出典データセット
uspto-grants-2013_01
特許番号
US08357706B2

反応ノート

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