Trifluoroacetic acid → 5-Bromo-6-cyclopropyl-3-iodopyridin-2-amine

HRID 531445Notes

Reaction equation

HRID 531445 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:11])=[N:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1.FC(F)(F)C(O)=O.[I:19]N1C(=O)CCC1=O>>[Br:1][C:2]1[CH:3]=[C:4]([I:19])[C:5]([NH2:11])=[N:6][C:7]=1[CH:8]1[CH2:9][CH2:10]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 900221395-Bromo-6-cyclopropylpyridin-2-amine

Product 1

HCID 900227685-Bromo-6-cyclopropyl-3-iodopyridin-2-amineYield 100%

Procedure

A solution of 5-bromo-6-cyclopropylpyridin-2-amine (2.1 g, 9.81 mmol), trifluoroaceticacid (170 mg, 1.47 mmol), N-iodosuccinimide (2.2 g, 9.81 mmol) stirred at room temperature for 30 minutes. Reaction mass was quenched with water, basified with ammonium hydroxide solution. Solid separated was filtered and dried to get 3.3 g (100% yield) of titled compound. 1H NMR (CDCl3, 300 MHz): δ 7.85 (s, 1H), 4.80-4.65 (bs, 2H), 2.39-2.25 (m, 1H), 1.0-0.90 (m, 4H). MS: m/z=338.9 (M+1).

Workup

  1. customReaction mass
  2. customwas quenched with water
  3. customSolid separated
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-1964b8422f8c46aebd9ca5d09c80cde2
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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