Ammonia → 2-tert-butyl-1H-pyrrolo[3,2-b]pyridin-5-amine

HRID 1043999Notes

Reaction equation

HRID 1043999 reaction equation
[C:1]([C:5]1[NH:13][C:12]2[C:7](=[N:8][C:9](Cl)=[CH:10][CH:11]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH3:15]>CO>[C:1]([C:5]1[NH:13][C:12]2[C:7](=[N:8][C:9]([NH2:15])=[CH:10][CH:11]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 579081952-tert-butyl-5-chloro-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 579081662-tert-butyl-1H-pyrrolo[3,2-b]pyridin-5-amineYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 500 mL autoclave, a solution of 2-tert-butyl-5-chloro-1H-pyrrolo[3,2-b]pyridine (5.0 g, 24 mmol) and CuSO4′5H2O (0.5 g, 2.0 mmol) in aqueous ammonia (200 mL) and CH3OH (100 mL) was heated at 180° C. (at this temperature, the pressure in the autoclave was about 2 MPa) and stirred for 10 hours. The mixture was allowed to cool down to room temperature. The solvent was removed by evaporation under vacuum. The resulting mixture was extracted with ethyl acetate (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum to give the crude product, which was purified by the preparative HPLC to give 2-tert-butyl-1H-pyrrolo[3,2-b]pyridin-5-amine (1.15 g, 26%). 1H NMR (CDCl3, 300 MHz) δ 10.63 (brs, 1H), 7.35 (d, J=8.7 Hz, 1H), 6.23 (d, J=8.7 Hz, 1H), 5.86 (d, J=1.5 Hz, 1H), 5.40 (brs, 2H), 1.29 (s, 9H); MS (ESI); m/e (M+H+): 190.2.

Workup

  1. customThe solvent was removed by evaporation under vacuum
  2. extractionThe resulting mixture was extracted with ethyl acetate (100 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. customevaporated under vacuum
  5. customto give the crude product, which
  6. customwas purified by the preparative HPLC

Sources & evidence

ORD record
ord-4dada1ff2a9346a3a98ddee88f5d55c4
Source dataset
uspto-grants-2013_10
Patent number
US08563573B2

Reaction notes

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