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Methyl iodide → (+/-)-tert-Butyl-4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-methoxyethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2174080
ノート
印刷プレビュー

反応式

HRID 2174080 の反応式
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([C:14]3[C:22]([O:23][CH3:24])=[CH:21][C:20]([CH3:25])=[C:19]4[C:15]=3[CH:16]=[CH:17][N:18]4[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])([OH:13])[CH3:12])=[N:8][C:7]=2[CH:33]=1)#[N:2].[CH3:34]I.[H-].[Na+]>CN(C=O)C>[C:29]([O:28][C:26]([N:18]1[C:19]2[C:15](=[C:14]([C:11]([C:9]3[O:10][C:6]4[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:33][C:7]=4[N:8]=3)([O:13][CH3:34])[CH3:12])[C:22]([O:23][CH3:24])=[CH:21][C:20]=2[CH3:25])[CH:16]=[CH:17]1)=[O:27])([CH3:32])([CH3:31])[CH3:30]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86701712tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-hydroxyethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

生成物 1

HCID 86701714(+/-)-tert-Butyl-4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-methoxyethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

反応条件

温度
0 °C

実験手順

To a solution of tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-hydroxyethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (250 mg, 0.559 mmol) in DMF (5.7 mL) at 0° C. was added successively MeI (0.105 mL, 1.676 mmol) and NaH (60% in mineral, 33.5 mg, 0.838 mmol). The reaction mixture was stirred at 0° C. for 1.5 h. The reaction mixture was quenched with 4 mL of saturated aq. solution of ammonium chloride and diluted with water and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-30% EtOAc:heptanes) to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.43 (dd, J=1.52, 0.63 Hz, 1H) 7.79-7.97 (m, 2H) 7.63 (d, J=3.79 Hz, 1H) 7.05 (d, J=3.79 Hz, 1H) 6.83 (s, 1H) 3.23 (s, 3H) 3.17 (s, 3H) 1.81-2.08 (m, 3H) 1.60 (s, 9H).

後処理

  1. customThe reaction mixture was quenched with 4 mL of saturated aq. solution of ammonium chloride
  2. additiondiluted with water and EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash chromatography (0-30% EtOAc:heptanes)

出典と根拠

ORDレコード
ord-ea928dca8d3345f599f048648cfb3bb8
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09056874B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート