Potassium Carbonate → HCID 86713616, compound

HRID 1618932Notes

Reaction equation

HRID 1618932 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]#[C:16][Si](C)(C)C.C(=O)([O-])[O-].[K+].[K+]>CO.C1COCC1>[Cl:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:13][CH2:14]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]#[CH:16]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 70978008HCID 70978008, compound

Product 1

HCID 86713616HCID 86713616, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-1-(cyclopropylmethyl)-5-[(trimethylsilyl)ethynyl]-1H-benzotriazole (0.72 g, 2.4 mmol) in MeOH (21 mL) and THF (2.1 mL) was treated with potassium carbonate (0.33 g, 2.4 mmol) and stirred for 18 hours. The mixture was concentrated in vacuo and the residue was dissolved in dichloromethane and washed with brine. The organic extracts were dried with magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (0-35% EtOAc in hexanes), providing the titled compound as a faint yellow oil: 1H-NMR (400 MHz, CDCl3) δ 7.60 (d, J=8.6 Hz, 1H), 7.43 (d, J=8.6 Hz, 1H), 4.52 (d, J=7.1 Hz, 2H), 3.44 (s, 1H), 1.36-1.43 (m, 1H), 0.66-0.71 (m, 2H), 0.48-0.52 (m, 2H) ppm; LRMS m/z (M+H) 234.1 [calculated for C12H11ClN3: 234.1].

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with brine
  4. dry with materialThe organic extracts were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel gradient chromatography (0-35% EtOAc in hexanes)

Sources & evidence

ORD record
ord-57e2d4667ac541a0be0a243734636df6
Source dataset
uspto-grants-2014_07
Patent number
US08772276B2

Reaction notes

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