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

HRID 1628019Notes

Reaction equation

HRID 1628019 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-d81a2e37314b4ef0b032f730cb945687
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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