Potassium Carbonate → HCID 68831017, compound

HRID 1783771Notes

Reaction equation

HRID 1783771 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)=O.O=P(Cl)(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[C:11]1([C:9]2[N:1]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]3=[CH:7][N:8]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 823699HCID 823699, compound

Product 1

HCID 68831017HCID 68831017, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of naphthalene-1-carboxylic acid (pyridin-2-ylmethyl)-amide (2.80 g, 10.7 mmol) in toluene (100 mL) was added POCl3 (9 mL). The mixture was heated to 90° C. for 12 h. After this time the mixture was allowed to cool and poured slowly into 10% aqueous potassium carbonate (500 mL). The mixture was extracted with ethyl acetate (2×100 mL) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica to yield 3-naphthalen-1-yl-imidazo[1,5-a]pyridine (1.89 g, 72%).

Workup

  1. temperatureto cool
  2. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  3. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-237717bf4dbc4636a0c4fa895c531924
Source dataset
uspto-grants-2009_03
Patent number
US07501438B2

Reaction notes

Loading…