4-Piperidinecarboxylic acid → 5-Bromo-7-fluoro-2-(piperidin-4-yl)benzo[d]oxazole

HRID 710077Notes

Reaction equation

HRID 710077 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([F:9])[C:3]=1[OH:10].[NH:11]1[CH2:19][CH2:18][CH:14]([C:15](O)=O)[CH2:13][CH2:12]1.[OH-].[Na+]>>[Br:8][C:6]1[CH:5]=[C:4]([F:9])[C:3]2[O:10][C:15]([CH:14]3[CH2:18][CH2:19][NH:11][CH2:12][CH2:13]3)=[N:1][C:2]=2[CH:7]=1

Participants

4

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 14798Sodium HydroxideHCID 27376372-Amino-4-bromo-6-fluorophenol

Product 1

HCID 710895515-Bromo-7-fluoro-2-(piperidin-4-yl)benzo[d]oxazoleYield 52.7%

Conditions

Temperature
195 °C

Procedure

2-amino-4-bromo-6-fluorophenol (1.7 g, 8.24 mmol) and isonipecotic acid (1.06 g, 8.24 mmol) were dissolved in polyphosphoric acid (28 g). This mixture was heated to 195° C. for 3 h. After 3 h, reaction mixture cooled to rt and basified with aqueous NaOH solution to pH 14. Solid that obtained was filtered and dried to obtain the title compound (1.3 g) as a brown solid.

Workup

  1. customreaction mixture
  2. customSolid that obtained
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-d6c02776a5a942dfb770966f1de5e44a
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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