2-Bromo-3-nitropyridine → 7-Bromo-6-azaindole

HRID 1643173Notes

Reaction equation

HRID 1643173 reaction equation
[Br:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:11]([Mg]Br)=[CH2:12]>C1COCC1>[Br:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:7]=1[NH:8][CH:12]=[CH:11]2

Participants

4

Reactant 2

HCID 5550542-Bromo-3-nitropyridineHCID 178418507HCID 178418507, compound

Product 1

HCID 196964567-Bromo-6-azaindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The route shown in Scheme 1 below exemplifies synthesis of certain 7-aryl(heteroaryl) and 7-anilino-6-azaindole-1-sulfonamide compounds of the present invention. 2-Bromo-3-nitropyridine (1) reacts with vinylmagnesium bromide in THF, at −40-50° C. to afford 7-Bromo-6-azaindole (2), which reacts with 4-methoxyphenylsulfonyl chloride to provide 7-bromo-1-(4-methoxyphenylsulfonyl)-1H-pyrrolo[2,3-c]pyridine (3). The sulfonamide (3), is then either treated with a substituted or unsubstituted phenylboronic acid, Pd(PPh3)4, and K2CO3 in toluene/EtOH to afford final compound (4) or treated with a substituted or unsubstituted aniline in pyridine to yield final compound (5).

Sources & evidence

ORD record
ord-dad6e93ffd904c25bf53b46c89e1485d
Source dataset
uspto-grants-2012_02
Patent number
US08119683B2

Reaction notes

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