4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 2-Ethoxy-5-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyridine

HRID 2090290Notes

Reaction equation

HRID 2090290 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.CC(C)([O-])C.[K+].Cl[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH3:31])=[N:27][CH:28]=1>C(O)(C)(C)C>[CH2:30]([O:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:12]2[CH:13]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]3)[CH:10]=[N:11]2)=[CH:28][N:27]=1)[CH3:31]

Participants

5

Reactant 3

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 105351905-(CHLOROMETHYL)-2-ETHOXYPYRIDINEHCID 23665647Potassium tert-butoxide

Product 1

HCID 594023392-Ethoxy-5-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyridine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

To a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.58 g, 3.0 mmol, Aldrich, Cat. 525057) in tert-butyl alcohol (5.0 mL) was added a solution of potassium tert-butoxide in tert-butyl alcohol (5.0 mL, 5.0 mmol, 1.00 M, Aldrich Cat. 331341). The reaction mixture was stirred at r.t. for 10 minutes followed by an addition of 5-(chloromethyl)-2-ethoxypyridine (0.54062 g, 3.15 mmol). The reaction mixture was stirred at 65° C. overnight. The reaction mixture was cooled to r.t., quenched with aqueous ammonium chloride, and extracted with EtOAc. The combined organic layers were washed with water and brine successively, dried with MgSO4, and concentrated. The residue was purified by flash chromatograph on a silica gel column using 20% ethyl acetate in methylene chloride as eluent to afford the desired compound. LCMS (M+H)+: m/z=330.4.

Workup

  1. stirringThe reaction mixture was stirred at 65° C. overnight
  2. temperatureThe reaction mixture was cooled to r.t.
  3. customquenched with aqueous ammonium chloride
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with water and brine successively
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatograph on a silica gel column

Sources & evidence

ORD record
ord-8f3ef6f38a214724ae47b6a9697fcfc6
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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