Potassium Carbonate → HCID 50996184, compound

HRID 872275Notes

Reaction equation

HRID 872275 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:15][CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:16].Cl[C:18]1[C:23]([C:24]#[N:25])=[CH:22][CH:21]=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:15][CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[O:16][C:18]1[C:23]([C:24]#[N:25])=[CH:22][CH:21]=[CH:20][N:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 810792-ChloronicotinonitrileHCID 67955772HCID 67955772, compound

Product 1

HCID 50996184HCID 50996184, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-bromo-1-(cyclobutylmethyl)-1H-benzotriazol-5-ol (3-5, 25 mg, 0.12 mmol, 1 equiv), 2-chloropyridine-3-carbonitrile (76 mg, 0.62 mmol, 5.0 equiv) and potassium carbonate (34 mg, 0.25 mmol, 5.0 equiv) in acetonitrile (3 mL) was irradiated at 170° C. in microwave reactor for 10 min. The mixture was purified by silica gel chromatography (0 to 100% ethyl acetate in hexanes) to give 2-{[4-bromo-1-(cyclobutylmethyl)-1H-benzotriazol-5-yl]oxy}pyridine-3-carbonitrile (1) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.26 (dd, 1H, J=4.9, 1.8 Hz), 8.08 (dd, 1H, J=7.3, 1.8 Hz), 7.54 (d, 1H, J=8.8 Hz), 7.39 (d, 1H, J=8.8 Hz), 7.15 (dd, 1H, J=7.3, 4.9 Hz), 4.66 (d, 2H, J=7.3 Hz), 3.00 (p, 1H, J=7.3 Hz), 2.11 (m, 2H), 1.92 (m, 4H) ppm. LRMS m/z (M+H) 386.0 found, 386.0 required.

Workup

  1. customwas irradiated at 170° C. in microwave reactor for 10 min
  2. customThe mixture was purified by silica gel chromatography (0 to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-830c866775624a4083291914bc086ddb
Source dataset
uspto-grants-2015_03
Patent number
US08975286B2

Reaction notes

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