Sodium hydride → 1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 4-(cyclohexylamino)-1-[[2-(trimethylsilyl)ethoxy]methyl]-, ethyl ester

HRID 1628019ノート

反応式

HRID 1628019 の反応式
[H-].[Na+].[CH:3]1([NH:9][C:10]2[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:13]=[C:12]3[NH:21][CH:22]=[CH:23][C:11]=23)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:24][Si:25]([CH2:28][CH2:29][O:30][CH2:31]Cl)([CH3:27])[CH3:26]>CN(C=O)C>[CH:3]1([NH:9][C:10]2[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:13]=[C:12]3[N:21]([CH2:31][O:30][CH2:29][CH2:28][Si:25]([CH3:27])([CH3:26])[CH3:24])[CH:22]=[CH:23][C:11]=23)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 58382222HCID 58382222、化合物

生成物 1

HCID 583819901H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 4-(cyclohexylamino)-1-[[2-(trimethylsilyl)ethoxy]methyl]-, ethyl ester収率 102.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

A suspension of NaH (60 wt % in mineral oil, 0.077 g, 1.9 mmol) in DMF (15 mL) was cooled to about 0° C. Ethyl 4-(cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.52 g, 1.8 mmol) was added and the resulting mixture was stirred for about 20 min at about 0° C. SEMCl (0.308 g, 1.84 mmol) was added and the resulting mixture was stirred for about 2 h while warming to rt. The solvent was removed under reduced pressure and the residue partitioned between EtOAc (120 mL) and saturated aqueous NH4Cl (40 mL). The organic phase was isolated, washed with brine (50 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give ethyl 4-(cyclohexylamino)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.77 g, 100%): LC/MS (Table 2, Method b) Rt=3.29 min.; MS m/z: 418 (M+H)+.

後処理

  1. stirringthe resulting mixture was stirred for about 2 h
  2. temperaturewhile warming to rt
  3. customThe solvent was removed under reduced pressure
  4. customthe residue partitioned between EtOAc (120 mL) and saturated aqueous NH4Cl (40 mL)
  5. customThe organic phase was isolated
  6. washwashed with brine (50 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-d81a2e37314b4ef0b032f730cb945687
出典データセット
uspto-grants-2014_07
特許番号
US08785639B2

反応ノート

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