Ammonia → Ethyl 1h-pyrrolo[3,2-c]pyridin4-ylcarbamate

HRID 230758Notes

Reaction equation

HRID 230758 reaction equation
[Na].C([N:9]1[C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:18][C:19](=[O:23])[O:20][CH2:21][CH3:22])[C:12]=2[CH:11]=[CH:10]1)C1C=CC=CC=1.N>C1COCC1>[NH:9]1[C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:18][C:19](=[O:23])[O:20][CH2:21][CH3:22])[C:12]=2[CH:11]=[CH:10]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 68825240HCID 68825240, compound

Product 1

HCID 68827324Ethyl 1h-pyrrolo[3,2-c]pyridin4-ylcarbamateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Sodium metal (0.067 g, 2.9 mmol, 10 eq) was added to a solution of ethyl 1-benzyl-1H-pyrrolo[3,2-c]pyridin-4-ylcarbamate (0.086 g, 0.29 mmol, 1.0 eq) in a mixture of liquid NH3 (5 mL) and THF (1 mL) at −78° C. The dark blue reaction mixture was stirred at −78° C. for 5 minutes and then was quenched with solid NH4Cl. The clear solution was allowed to warm to room temperature, treated with 10% NaHCO3 and extracted with 10/1 CHCl3/MeOH. The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford the product (0.059 g, 100%) as a solid. 1H NMR (CD3OD) δ 7.74 (d, 1H, J=6.0 Hz), 7.21 (d, 1H, J=3.4 Hz), 7.09 (d, 1H, J=5.7Hz), 6.59 (d, 1H, J=3.4Hz), 4.15 (q, 2H, J=7.1 Hz), 1.25 (t, 3H, J=7.1 Hz); MS(ESI+) m/z 206 (M+H)+. Calculated: 206.0930, found: 206.0932.

Workup

  1. customThe dark blue reaction mixture
  2. customwas quenched with solid NH4Cl
  3. temperatureto warm to room temperature
  4. additiontreated with 10% NaHCO3
  5. extractionextracted with 10/1 CHCl3/MeOH
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c377e02dcfb441a8ac1051c328e0d7c
Source dataset
uspto-grants-2009_07
Patent number
US07566784B2

Reaction notes

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