Potassium Phosphate, Tribasic → 1-{2-(2-Methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenoxymethyl)-3-trimethylsilylethynyl-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one

HRID 628519Notes

Reaction equation

HRID 628519 reaction equation
Br[C:2]1[C:3]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]3[C:27]([CH3:28])=[C:26]([CH3:29])[C:25]([CH3:30])=[N:24]3)=[CH:19][C:18]=2[CH3:31])=[C:4]([N:8]2[C:12](=[O:13])[N:11]([CH3:14])[N:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:32][Si:33]([C:36]#[CH:37])([CH3:35])[CH3:34].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O.O1CCOCC1>[CH3:31][C:18]1[CH:19]=[C:20]([N:23]2[C:27]([CH3:28])=[C:26]([CH3:29])[C:25]([CH3:30])=[N:24]2)[CH:21]=[CH:22][C:17]=1[O:16][CH2:15][C:3]1[C:2]([C:37]#[C:36][Si:33]([CH3:35])([CH3:34])[CH3:32])=[CH:7][CH:6]=[CH:5][C:4]=1[N:8]1[C:12](=[O:13])[N:11]([CH3:14])[N:10]=[N:9]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 66111TrimethylsilylacetyleneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 1182365091-{3-Bromo-2-[2-methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one

Product 1

HCID 1238857971-{2-(2-Methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenoxymethyl)-3-trimethylsilylethynyl-phenyl}-4-methyl-1,4-dihydrotetrazole-5-oneYield 32.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-{3-bromo-2-[2-methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 70) 0.3 g, trimethylsilylacetylene 0.2 g, tetrakis triphenylphosphine palladium 0.05 g, tri-tert-butylphosphine 0.07 g, potassium phosphate 0.6 g, 1,4-dioxane 5 ml and water 0.5 ml was stirred at 100° C. for five hours. After cooling, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and was dried over anhydrous magnesium sulfate and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-{2-[2-methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenoxymethyl]-3-trimethylsilylethynyl-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one 0.1 g.

Workup

  1. temperatureAfter cooling
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated saline
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-37d23356c73445829901575095af49a8
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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