Imidazole → 4-(2-Triisopropylsilanyloxy-ethylamino)-nicotinonitrile

HRID 2264914ノート

反応式

HRID 2264914 の反応式
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[C:10]([C:11]#[N:12])=[CH:9][N:8]=[CH:7][CH:6]=1.N1C=CN=C1.[CH:18]([Si:21](Cl)([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19]>CN(C=O)C>[CH:18]([Si:21]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:1][CH2:2][CH2:3][NH:4][C:5]1[C:10]([C:11]#[N:12])=[CH:9][N:8]=[CH:7][CH:6]=1)([CH3:20])[CH3:19]

参加物

5

反応物 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 59596532HCID 59596532、化合物

生成物 1

HCID 595964584-(2-Triisopropylsilanyloxy-ethylamino)-nicotinonitrile収率 77%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-(2-hydroxy-ethylamino)-nicotinonitrile (500 mg, 3.07 mmol) and imidazole (250 mg, 3.68 mmol) in DMF (15 mL) was added triisopropylsilyl chloride (0.723 mL, 3.37 mmol). The reaction mixture stirred at room temperature for 2 hours. The mixture was then partitioned between ethyl acetate and water, the organic layer isolated and washed with brine, dried (Na2SO4), filtered and concentrated. The resultant residue was purified by flash chromatography (Si-PPC, pentane:ether, gradient 50:50 to 30:70) to provide the title compound as a white solid (753 mg, 77%). LCMS (method B): RT=2.92 min, M+H+=320.

後処理

  1. customThe mixture was then partitioned between ethyl acetate and water
  2. customthe organic layer isolated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant residue was purified by flash chromatography (Si-PPC, pentane:ether, gradient 50:50 to 30:70)

出典と根拠

ORDレコード
ord-bb9d240a7c964ce4a65cce478075a9e2
出典データセット
uspto-grants-2010_12
特許番号
US07855216B2

反応ノート

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