2-Chloro-5-fluoro-3-nitropyridine → 7-Chloro-4-fluoro-1H-pyrrolo[2,3-C]pyridine

HRID 2184253Notes

Reaction equation

HRID 2184253 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([F:11])=[CH:4][N:3]=1.[CH:12]([Mg]Br)=[CH2:13]>>[F:11][C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[C:7]2[C:6]=1[CH:12]=[CH:13][NH:8]2

Participants

3

Reactant 2

HCID 107736262-Chloro-5-fluoro-3-nitropyridineHCID 178418507HCID 178418507, compound

Product 1

HCID 224762857-Chloro-4-fluoro-1H-pyrrolo[2,3-C]pyridine

Procedure

The chemistry in Scheme 3 provided the derivatives which corresponds to general formula 5 and has a 6-aza ring and R2=F and R4=Cl. In particular, reaction of 2-chloro-5-fluoro-3-nitro pyridine with 3 equivalents of vinyl Magnesium bromide using the typical conditions described herein will provide 4-fluoro-7-chloro-6-azaindole in high yield. Addition of this compound to a solution of aluminum trichloride in dichloromethane stirring at ambident temperature followed 30 minutes later with chloromethyl or chloroethyl oxalate provided an ester. Hydrolysis with KOH as in the standard procedures herein provided an acid salt which reacted with piperazines 4 (for example 1-benzoyl piperazine) in the presence of DEPBT under the standard conditions described herein to provide the compound 5 described just above. The compound with the benzoyl piperazine is N-(benzoyl)-N′-[(4-fluoro-7-chloro-6-azaindol-3-yl)-oxoacetyl]-piperazine and is compound 5av. The compound with the (R)-methyl benzoyl piperazine is 5 av′(R)-N-(benzoyl)-3-methyl-N′-[(4-fluoro-7-chloro-6-azaindol-3-yl)-oxoacetyl]-piperazine and is compound 5av′

Workup

  1. customThe chemistry in Scheme 3 provided the derivatives which

Sources & evidence

ORD record
ord-7343f9837bdc44b6ad622e4f5a67254e
Source dataset
uspto-grants-2005_05
Patent number
US06900323B2

Reaction notes

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