1-AMINOPYRIDIN-2(1H)-ONE → HCID 10017794, compound

HRID 2213103Notes

Reaction equation

HRID 2213103 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[C:6]#[N:7].[NH2:17][N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]1=O.CC(C)([O-])C.[K+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[N:7]=[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][N:18]3[N:17]=2)[CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 44161921-AMINOPYRIDIN-2(1H)-ONEHCID 21956523HCID 21956523, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10017794HCID 10017794, compound

Conditions

Temperature
115 °C

Procedure

3-methyoxy-4-pyridin-2-ylbenzonitrile (104 mg, 0.95 mmol) and 1-aminopyridin-2(1H)-one (198 mg, 0.95 mmol) were dissolved in a solution of potassium t-butoxide (2 mL of 1M in t-butanol, 2.0 mmol). The reaction mixture was heated to 115° C. for 1 h, cooled and concentrated. The residue was purified by flash column chromatography on silica gel eluting with MeOH:CH2Cl2 (1:19) to afford the desired 2-(3-methoxy-4-pyridin-2-ylphenyl)[1,2,4]triazolo[1,5-a]pyridine. 1H NMR (CDCl3, 300 MHz) δ 8.75 (m, 1H), 8.64 (d, 1H), 8.06 (dd, 1H), 7.97 (s, 1H), 7.94 (m, 2H), 7.81 (d, 1H), 7.74 (dt, 1H), 7.55 (m, 1H), 7.25 (m, 1H), 7.05 (dt, 1H), 4.03 (s, 3H) ppm. 3C NMR (CDCl3, 75 MHz) δ 163.8, 157.2, 155.5, 151.7, 149.4, 135.7, 132.2, 131.5, 130.6, 129.6, 128.3, 125.2, 121.9, 120.0, 116.4, 113.8, 110.0, 55.8 ppm. MS (ESI) 303 (M)+.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe residue was purified by flash column chromatography on silica gel eluting with MeOH:CH2Cl2 (1:19)

Sources & evidence

ORD record
ord-e0104994fa994e93977ae6dca39b6aea
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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