Sulfur → 3-Bromo-4-cyclopropyl-5-fluoropyridine

HRID 530013Notes

Reaction equation

HRID 530013 reaction equation
[Br:1][C:2]1[CH:7]([CH:8]2[CH2:10][CH2:9]2)[C:6]([F:11])=[CH:5][N:4](C(OC2C=CC=CC=2)=O)[CH:3]=1.[S]>C1C2C(CCCC2)CCC1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:11])[C:7]=1[CH:8]1[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 5362487SulfurHCID 867296503-Bromo-4-cyclopropyl-5-fluoro-4H-pyridine-1-carboxylic acid phenyl ester

Product 1

HCID 717433633-Bromo-4-cyclopropyl-5-fluoropyridine

Reagents, catalysts & solvents 1

HCID 7044DecalinSolvent

Procedure

A mixture of the crude phenyl 3-bromo-4-cyclopropyl-5-fluoropyridine-1 (4H)-carboxylate (1.14 g, 0.0034 mol) and sulphur (0.108 g, 0.0034 mol) were heated at reflux in DECALIN (10 mL) for a period of 3 h, then cooled to room temperature. Purification by silica gel chromatography, eluting first with hexanes, then with a 2-5% ethyl acetate-hexane gradient, gave the title compound. MS (M+1): 217.1.

Workup

  1. temperaturewere heated
  2. customPurification by silica gel chromatography
  3. washeluting first with hexanes

Sources & evidence

ORD record
ord-4539eedb92d947328275f419d474cd99
Source dataset
uspto-grants-2016_05
Patent number
US09351973B2

Reaction notes

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