Bromocyclopentane → 1-cyclopentyl-5-fluoro-3-iodo-1H-indazole

HRID 868856Notes

Reaction equation

HRID 868856 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[I:11].Br[CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>>[CH:13]1([N:7]2[C:8]3[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)[C:5]([I:11])=[N:6]2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 8728BromocyclopentaneHCID 178505475HCID 178505475, compound

Product 1

HCID 867231461-cyclopentyl-5-fluoro-3-iodo-1H-indazoleYield 71%

Procedure

The title compound was prepared in 71% yield from 5-fluoro-3-iodo-indazole and bromocyclopentane according to the procedure for Preparation 11A. The minor isomer was not isolated cleanly. 1H NMR (400 MHz, CDCl3): δ 1.69-1.76 (2H, m), 1.92-1.98 (2H, m), 2.12-2.18 (4H, m), 4.87-4.95 (1H, m), 7.08 (1H, dd, J=8.2, 2.3 Hz), 7.17 (1H, td, J=8.9, 2.4 Hz), 7.35 (1H, dd, J=9.1, 4.0 Hz). [M+H] calc'd for C12H12FIN2, 331; found 331.

Workup

  1. customThe minor isomer was not isolated cleanly

Sources & evidence

ORD record
ord-d6abe61725ac4fd5b98096a8a1a8c4c5
Source dataset
uspto-grants-2015_03
Patent number
US08969343B2

Reaction notes

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