4'-Fluoroacetophenone → HCID 68901665, compound

HRID 735335Notes

Reaction equation

HRID 735335 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[CH:4]=O.[CH3:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=O.[OH-].[K+]>C(O)C>[Br:10][C:7]1[CH:6]=[C:3]2[C:2](=[N:9][CH:8]=1)[N:1]=[C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH:11]=[CH:4]2

Participants

5

Reactant 3

HCID 98284'-FluoroacetophenoneHCID 14797Potassium HydroxideHCID 242137922-Amino-5-bromo-3-pyridinecarbaldehyde

Product 1

HCID 68901665HCID 68901665, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-5-bromonicotinaldehyde [prepared by the method of Duggan et al., WO 9818461] (5.53 g, 27.5 mmol), 4-fluoroacetophenone (3.0 mL, 24.8 mmol) and 20% aqueous potassium hydroxide (3.5 mL) in ethanol (400 mL) was heated at reflux for 1 hour. The reaction mixture was allowed to stand at room temperature, the crystals formed collected under suction, washed with ethanol and dried in vacuo to afford 6-bromo-2-(4-fluorophenyl)-1,8-naphthyridine (4.86 g, 65%). 1H NMR (500 MHz, CDCl3) δ 9.12 (1H, d, J 2.5 Hz), 8.34 (1H, d, J 2.5 Hz), 8.32-8.28 (2H, m), 8.18 (1H, d, J 8.5 Hz), 7.99 (1H, d, J 8.5 Hz), 7.25-7.19 (2H, m).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. customto stand at room temperature
  4. customthe crystals formed
  5. customcollected under suction
  6. washwashed with ethanol
  7. customdried in vacuo

Sources & evidence

ORD record
ord-fce5798131044bcdab11a8e29f125860
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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