Water → HCID 18446584, compound

HRID 1868302Notes

Reaction equation

HRID 1868302 reaction equation
[C:1]1([C:7]2[S:8][C:9]3[CH:14]=[CH:13][NH:12][C:11](=[O:15])[C:10]=3[N:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:17]Br.O>C(O)(=O)C>[Br:17][C:14]1[C:9]2[S:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:16][C:10]=2[C:11](=[O:15])[NH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 18446527HCID 18446527, compound

Product 1

HCID 18446584HCID 18446584, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-phenyl-5H-thiazolo[4,5-c]pyridin-4-one 44 (400 mg, 1.75 mmol) in acetic acid (5 mL) at rt was treated with bromine (320 mg, 1.93 mmol) and the resulting mixture was heated at reflux for 30 min. After cooling to rt, water (20 mL) was added to the mixture. The yellow solid which formed was filtered, washed with water and dried in the air to afford 45 (527 mg). 1H NMR (400 MHz, d6-DMSO) δ: 7.57 (m, 3H), 7.70 (s, 1H), 8.05 (m, 2H), MS (EI) m/z (M+H+) 308.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 30 min
  3. customThe yellow solid which formed
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried in the air

Sources & evidence

ORD record
ord-3fca2422de284da38002c9759831bf01
Source dataset
uspto-grants-2009_12
Patent number
US07635695B2

Reaction notes

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