2-Pyridinecarboxaldehyde → HCID 78023548, compound

HRID 2366577Notes

Reaction equation

HRID 2366577 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[O:16][CH2:15][CH2:14][C:13]3=[O:20])=[CH:6][CH:5]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:29]=O.N1CCCC1>C(O)C>[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:29]=[C:14]1[C:13](=[O:20])[C:12]2[C:17](=[CH:18][CH:19]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:21])[F:22])=[CH:9][CH:8]=3)[CH:11]=2)[O:16][CH2:15]1

Participants

5

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 31268PyrrolidineHCID 71183601HCID 71183601, compound

Product 1

HCID 78023548HCID 78023548, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 400 mg 6-(4-(trifluoromethoxy)phenyl)chroman-4-one (1.3 mmol, 1.0 eq), 150 μL 2-pyridine carboxaldehyde (1.6 mmol, 1.2 eq) and 130 μL pyrrolidine (1.6 mmol, 1.2 eq) in 10 mL ethanol was refluxed 3 h. The reaction was concentrated and purified on silica gel column eluting with EA:Hex. 160 mg of a yellow solid was collected. m/z=398.0

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified on silica gel column
  3. washeluting with EA
  4. custom160 mg of a yellow solid was collected

Sources & evidence

ORD record
ord-8995d81b390c4d86b34714586e5f4bd1
Source dataset
uspto-grants-2014_04
Patent number
US08697863B2

Reaction notes

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