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Potassium Carbonate → 1-(2-{[4-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-yl]oxy}pyridin-3-yl)ethanone

HRID 872276
Notes
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Reaction equation

HRID 872276 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:16].[C:17]([C:20]1[C:21](F)=[N:22][CH:23]=[CH:24][CH:25]=1)(=[O:19])[CH3:18].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][C:12]([CH3:13])([CH3:15])[CH3:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:16][C:21]1[C:20]([C:17](=[O:19])[CH3:18])=[CH:25][CH:24]=[CH:23][N:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127111221-(2-Fluoropyridin-3-yl)ethan-1-oneHCID 574249954-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol

Product 1

HCID 509965401-(2-{[4-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-yl]oxy}pyridin-3-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6342Acetonitrile
Solvent

Procedure

4-Bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol (1-6) (1 g, 3.52 mmol, 1.0 equiv.), 3-acetyl-2-fluoropyridine (0.979 g, 7.04 mmol, 2.0 equiv.) and potassium carbonate (0.973 g, 7.04 mmol, 2.0 equiv.) were dissolved in acetonitrile (10 ml). The mixture was irradiated at 200° C. in microwave reactor until LCMS showed mostly desired product. The solvent was evaporated in vacuo, the mixture was neutralized with saturated aqueous NH4Cl, and then extracted with EtOAc. The organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (EtOAc/Hexane gradient from 0 to 100%) to obtain 2. 1H NMR (CDCl3) δ 8.30-8.24 (1H, m), 8.24 (1H, s), 7.83 (1H, d, J=2.06 Hz), 7.56 (1H, d, J=8.91 Hz), 7.29 (1H, dd, J=2.1, 8.9 Hz), 7.16-7.10 (1H, m), 4.42 (2H, s), 2.80 (3H, s), 1.09 (9H, s) ppm. LRMS m/z (M+H) 403.0 and 405.0 (intensity ratio ˜1:1) found, 403.1 and 405.1 required.

Workup

  1. customThe mixture was irradiated at 200° C. in microwave reactor until LCMS

Sources & evidence

ORD record
ord-82d95ec3d6994303be95beb39ca06f08
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08975286B2

Reaction notes

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