Potassium Carbonate → HCID 10158642, compound

HRID 899390Notes

Reaction equation

HRID 899390 reaction equation
[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([O:10][C:11]3[N:30]=[CH:29][CH:28]=[CH:27][C:12]=3[C:13]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23](O)([CH3:25])[CH3:24])=[CH:19][CH:18]=3)=[O:14])[CH:7]=[CH:6][C:5]=12.C[Si]([C:35]#[N:36])(C)C.[Sn](Cl)(Cl)(Cl)Cl.C(=O)([O-])[O-].[K+].[K+].O.O.[F-].[K+]>ClCCl.O>[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([O:10][C:11]3[N:30]=[CH:29][CH:28]=[CH:27][C:12]=3[C:13]([NH:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]([C:35]#[N:36])([CH3:25])[CH3:24])=[CH:21][CH:22]=3)=[O:14])[CH:7]=[CH:6][C:5]=12

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 24287Tin tetrachlorideHCID 82115Trimethylsilyl cyanideHCID 9865929CP-612372HCID 23708904Potassium fluoride dihydrate

Product 1

HCID 10158642HCID 10158642, compoundYield 40.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(benzo[2,1,3]oxadiazol-5-yloxy)-N-[4-(1-hydroxy-1-methyl-ethyl)-benzyl]-nicotinamide (300 mg, 0.74 mmol) in dichloromethane (1.5 ml) cooled to 0° C. was added trimethylsilyl cyanide (1 ml, 7.4 mmol) followed by slow addition of tin tetrachloride (7 drops of a 1.0 M solution in dichloromethane). The reaction mixture was allowed to warm to room temperature overnight. Potassium carbonate (300 mg, 2.10 mmol) and potassium fluoride dihydrate (120 mg, 2.10 mmol) were added, followed by dropwise addition of water. The reaction mixture was stirred vigorously for 90 m., after which silica gel was (600 mg) added. The mixture was filtered and washed thoroughly with dichloromethane. The filtrate was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated to give 124 mg of a pale yellow solid. Product was recrystallized from ethyl acetate/hexane to afford 96 mg (31% yield) of a pale yellow solid.

Workup

  1. additionadded
  2. filtrationThe mixture was filtered
  3. washwashed thoroughly with dichloromethane
  4. washThe filtrate was washed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a64eaedaea9147e98dd4d01ceb404108
Source dataset
uspto-grants-2008_04
Patent number
US07354941B2

Reaction notes

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