Pyridine → HCID 69369980, compound

HRID 724393Notes

Reaction equation

HRID 724393 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:17]=[C:16]3[C:12]([C:13]([CH:18]=[CH:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:14][NH:15]3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[C:32](OC(=O)C)(=[O:34])[CH3:33]>ClCCl.O>[C:32]([NH:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:17]=[C:16]3[C:12]([C:13]([CH:18]=[CH:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:14][NH:15]3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1)(=[O:34])[CH3:33]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 69370587HCID 69370587, compound

Product 1

HCID 69369980HCID 69369980, compoundYield 129.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 6-(3-aminophenylsulfanyl)-3-styryl-1H-indazole (43.7 mg, 0.10 mmol) in dichloromethane (0.5 mL) was added pyridine (81 μL, 1.0 mmol, 10 equiv), and acetic anhydride (47 μL, 0.5 mmol, 5 equiv). The mixture was allowed to stir for 10 min at 23° C. The mixture was diluted with water and the product was extracted with 30% hexane in ethyl acetate. The organic material was washed with 5% citric acid and saturated sodium bicarbonate. The organic material was dried over sodium sulfate, decanted and concentrated. Purification by silica gel chromatography (3:7 ethyl acetate-hexane) gave 6-(3-acetamido-phenylsulfanyl)-3-styryl-1H-indazole as an oil (50 mg, 97%): Rf sm 0.33, Rf p 0.18 (ethyl acetate-hexane 3:7); 1H NMR (300 MHz, CDCl3) δ 7.94 (d, 1H), 7.65–7.1 (m, 13H), 5.70 (s, 2H), 3.62 (t, 2H, J=8.2 Hz), 2.18 (s, 3H), 0.93 (t, 2H, J=8.2 Hz), −0.05 (s, 9H). HRMS (FAB) [M+Cs]/z Calc'd 648.1117. found 648.1098.

Workup

  1. extractionthe product was extracted with 30% hexane in ethyl acetate
  2. washThe organic material was washed with 5% citric acid and saturated sodium bicarbonate
  3. dry with materialThe organic material was dried over sodium sulfate
  4. customdecanted
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (3:7 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-858ba53de1dd4e51ab319d4b522e09f8
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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