2-((Phenylmethoxy)methyl)-5-(tributylstannyl)-2H-tetrazole → HCID 24959329, compound

HRID 2381821Notes

Reaction equation

HRID 2381821 reaction equation
Br[C:2]1[S:3][C:4]([C:8]([NH:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:9])=[C:5]([CH3:7])[N:6]=1.[CH2:18]([O:25][CH2:26][N:27]1[N:31]=[N:30][C:29]([Sn](CCCC)(CCCC)CCCC)=[N:28]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:18]([O:25][CH2:26][N:27]1[N:31]=[N:30][C:29]([C:2]2[S:3][C:4]([C:8]([NH:10][CH2:11][C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)=[O:9])=[C:5]([CH3:7])[N:6]=2)=[N:28]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 2

HCID 113405612-((Phenylmethoxy)methyl)-5-(tributylstannyl)-2H-tetrazoleHCID 666315502-Bromo-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

Product 1

HCID 24959329HCID 24959329, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 2-bromo-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide (0.10 g, 0.32 mmol), copper(I) iodide (0.002 g, 0.009 mmol), tetrakis(triphenylphosphine)palladium(0) (0.011 g, 0.009 mmol) in anhydrous toluene (3 mL) was added 2-(benzyloxymethyl)-5-(tributylstannyl)-2H-tetrazole (0.018 g, 0.39 mmol, prepared following the procedure described in Tetrahedron Letters, 41, (2000), 2805-2809) and the reaction mixture was heated at 85° C. in a sealed tube for 6 hours. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate:methanol, 10:1) to afford the title compound as a clear oil (0.065 g, 48%): 1H NMR (300 MHz, CDCl3) δ 8.53 (br s, 1H), 8.52-8.45 (m, 1H), 7.75-7.69 (m, 1H), 7.36-7.20 (m, 6H), 6.80 (t, J=5.8 Hz, 1H), 5.97 (s, 2H), 4.69 (s, 2H), 4.61 (d, J=5.8 Hz, 2H), 2.72 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 161.4, 160.3, 157.3, 153.3, 149.2, 149.1, 135.9, 135.3, 133.5, 128.7, 128.5, 128.2, 128.0, 123.8, 80.3, 72.4, 41.7, 17.5; MS (ES+) m/z 422.3 (M+1).

Workup

  1. customprepared
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography (ethyl acetate:methanol, 10:1)

Sources & evidence

ORD record
ord-7052e434178b4526a9c881f5e2a77b86
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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