Methyl iodide → HCID 86701779、化合物

HRID 2174133ノート

反応式

HRID 2174133 の反応式
[C:1]([CH2:3][C:4]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([CH3:15])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])#[N:2].CI.[CH3:25][Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[C:1]([CH:3]([C:4]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([CH3:15])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:25])#[N:2]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 86701770HCID 86701770、化合物

生成物 1

HCID 86701779HCID 86701779、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

tert-Butyl 4-(cyanomethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 155-B) (1.2 g, 4.00 mmol) was dissolved in THF (40.0 ml), MeI (0.300 ml, 4.79 mmol) was then added at −78° C. At this point, lithium bis(trimethylsilyl)amide (4.39 ml, 4.39 mmol) was added and the reaction stirred for 10 minutes. The reaction was then quenched at −78° C. with a saturated aq. solution of ammonium chloride, diluted with water and EtOAc and the layers were separated. The organic layer was dried over Na2SO4 and concentrated and purified via FCC (0-50% EtOAc:heptanes) to obtain the title compound. MS (ESI+) m/z 313.5 (M−H).

後処理

  1. customThe reaction was then quenched at −78° C. with a saturated aq. solution of ammonium chloride
  2. additiondiluted with water and EtOAc
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified via FCC (0-50% EtOAc:heptanes)

出典と根拠

ORDレコード
ord-a4db3995feb54c998771a7a3f31a087c
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

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