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

HRID 1016492Notes

Reaction equation

HRID 1016492 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-ec1e68a5f12d4afda2889659baf172d1
Source dataset
uspto-grants-2002_11
Patent number
US06476034B2

Reaction notes

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