Sodium hydride → (S)-1-(2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-5-methyl-1H-indole-2-carbonitrile

HRID 1505664ノート

反応式

HRID 1505664 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]#[N:12])=[CH:5]2.[H-].[Na+].Cl[CH2:16][C@@H:17]([CH2:26][O:27][Si:28]([CH3:34])([CH3:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[O:18][Si:19]([CH3:25])([CH3:24])[C:20]([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C.O>[Si:19]([O:18][C@H:17]([CH2:26][O:27][Si:28]([C:29]([CH3:30])([CH3:32])[CH3:31])([CH3:33])[CH3:34])[CH2:16][N:7]1[C:8]2[C:4](=[CH:3][C:2]([CH3:1])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:11]#[N:12])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:25])[CH3:24]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 199947895-methyl-1H-indole-2-carbonitrileHCID 90405653(R)-5-(chloromethyl)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecane

生成物 1

HCID 90405548(S)-1-(2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-5-methyl-1H-indole-2-carbonitrile収率 48.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 39 mg of 5-methyl-1H-indole-2-carbonitrile (0.25 mmol) in 0.5 mL of DMF 15 mg of NaH (60% in oil, 0.375 mmol) was added and mixture was stirred for 30 min. Then 170 mg of (R)-5-(chloromethyl)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecane (0.5 mmol) was added and stirring continued for 24 hs. The reaction mixture was diluted with 10 mL of water and extracted with DCM. Combined organic extracts dried over sodium sulfate, concentrated and purified using silica gel column eluting with hexane-ethyl acetate 50:1 to afford 56 mg of (S)-1-(2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-5-methyl-1H-indole-2-carbonitrile. 1H NMR (600 MHz, CDCl3): δ 8.09 (d, 1H, J=8.8 Hz), 7.35 (s, 1H), 7.24 (d, 1H, J=8.8 Hz), 7.18 (s, 1H), 4.04 (m, 1H), 3.82 (m, 1H), 3.77 (m, 2H), 3.68 (m, 1H), 2.43 (s, 3H), 1.08 (m, 18H), 0.26 (m, 12H).

後処理

  1. stirringstirring
  2. extractionextracted with DCM
  3. dry with materialCombined organic extracts dried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified
  6. washeluting with hexane-ethyl acetate 50:1

出典と根拠

ORDレコード
ord-60fcfde04cc742eea7d744f2aae105c8
出典データセット
uspto-grants-2015_12
特許番号
US09216993B2

反応ノート

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