Ammonia → 1H-pyrrolo[2,3-c]pyridin-7-amine

HRID 1173108Notes

Reaction equation

HRID 1173108 reaction equation
N.Br[C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[CH:11]=[CH:10][NH:9][C:8]=12.BrC1C([N+]([O-])=O)=CC=C[N:14]=1>[Cu]>[NH2:14][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[CH:11]=[CH:10][NH:9][C:8]=12

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5550542-Bromo-3-nitropyridineHCID 196964567-Bromo-6-azaindole

Product 1

HCID 190801861H-pyrrolo[2,3-c]pyridin-7-amine

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
120 °C

Procedure

To 84 ml of aqueous concentrated ammonia were added 600 mg (3.05 mmol) of 7-bromo-1H-pyrrolo[2,3-c]pyridine synthesized from 2-bromo-3-nitropyridine in the same manner as in Production Example 1a, 194 mg of a copper powder and 603 mg of cuprous chloride. The mixture was heated in a sealed tube at 120° C. for 15 hours and then treated, to give 170 mg of 7-amino-1H-pyrrolo[2,3-c]pyridine. The resulting product was reacted and treated in the same manner as in Examples 1a and 2a, to give 57 mg of the title compound.

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-1984b068d707462f827e7c0a08a19cc2
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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