Sodium Bicarbonate → ethyl 3-amino-7-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

HRID 2264925Notes

Reaction equation

HRID 2264925 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][C:3]=1[Cl:10].Cl.[CH2:12]([O:14][C:15](=[O:18])[CH2:16][NH2:17])[CH3:13].C(=O)([O-])O.[Na+]>>[CH2:12]([O:14][C:15]([C:16]1[NH:17][C:2]2[C:3]([Cl:10])=[CH:4][N:5]=[CH:6][C:7]=2[C:8]=1[NH2:9])=[O:18])[CH3:13]

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 197757134,5-Dichloronicotinonitrile

Product 1

HCID 59596637ethyl 3-amino-7-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

Procedure

A mixture of 4,5-dichloronicotinonitrile (3.0 g, 17.3 mmol), glycine ethyl ester hydrochloride (7.2 g, 52.0 mmol) and sodium hydrogen carbonate (9.06 g, 104 mmol) in IMS (50 ml) was heated at reflux for 16 hours. The cooled reaction mixture was then partitioned between ethyl acetate and water, the organic layer washed with water then brine, dried (MgSO4) filtered and concentrated in vacuo. The resultant residue was triturated in diethyl ether to give the title compound as a buff solid (3.58 g, 86%). 1H NMR (CDCl3) 8.80 (1H, s), 8.36 (1H, s), 4.97 (2H, s, br), 4.44 (2H, q, J=7.0 Hz), 1.44 (3H, t, J=7.0 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. customThe cooled reaction mixture
  4. customwas then partitioned between ethyl acetate and water
  5. washthe organic layer washed with water
  6. dry with materialbrine, dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resultant residue was triturated in diethyl ether

Sources & evidence

ORD record
ord-3e17bd967c1e4fa082fa719d48aafdcb
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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