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

HRID 1628019노트

반응식

HRID 1628019 반응식
[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

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 58382222HCID 58382222, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-d81a2e37314b4ef0b032f730cb945687
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785639B2

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