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

HRID 717541Notes

Reaction equation

HRID 717541 reaction equation
C1(OC([N:10]2[CH:15]=[C:14]([F:16])[CH:13]([CH:17]3[CH2:19][CH2:18]3)[C:12]([Br:20])=[CH:11]2)=O)C=CC=CC=1.[S]>C1C2C(CCCC2)CCC1>[Br:20][C:12]1[CH:11]=[N:10][CH:15]=[C:14]([F:16])[C:13]=1[CH:17]1[CH2:18][CH2:19]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 crude 3-bromo-4-cyclopropyl-5-fluoro-4H-pyridine-1-carboxylic acid phenyl ester (A; 7.5 g, 0.022 mol) and sulphur (0.71 g, 0.022 mol) were heated at reflux in DECALIN (25 mL) for a period of 3 h and then cooled to RT. The reaction mixture was purified by silica gel column chromatography, eluting first with hexane and then with a 2-5% ethyl acetate-hexane gradient to afford 3-bromo-4-cyclopropyl-5-fluoro-pyridine. 1H NMR (400 MHz, DMSO-d6) δ 8.54 (s, 1H), 8.42 (s, 1H), 1.98-1.94 (m, 1H), 1.11-1.09 (m, 2H), 0.99-0.98 (m, 2H). MS (M+1): 217.1.

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography
  2. washeluting first with hexane

Sources & evidence

ORD record
ord-5ba2ee9dba564c71a4b1c909d838a790
Source dataset
uspto-grants-2015_11
Patent number
US09193724B2

Reaction notes

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