HCID 12137495, compound → HCID 12137496, compound

HRID 985369Notes

Reaction equation

[I-].[CH:2](P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([CH3:4])[CH3:3].C([Li])CCC.[CH3:29][C:30]1[CH:35]=[C:34]([C:36]#[C:37][CH:38]=O)[N:33]=[C:32]([O:40][C:41]2[N:45]([CH3:46])[N:44]=[C:43]([C:47]([F:50])([F:49])[F:48])[CH:42]=2)[CH:31]=1>C1COCC1>[CH3:29][C:30]1[CH:35]=[C:34]([C:36]#[C:37][CH:38]=[C:2]([CH3:4])[CH3:3])[N:33]=[C:32]([O:40][C:41]2[N:45]([CH3:46])[N:44]=[C:43]([C:47]([F:50])([F:49])[F:48])[CH:42]=2)[CH:31]=1

Participants

Conditions

Temperature: -70 °C

Procedure

A mixture of isopropyltriphenylphosphine iodide (0.43 g, 1 mmol) in a dry THF (15 ml) is cooled to −70° C. under an inert gas atmosphere. A 2.5 M solution of butyl lithium (0.44 ml) is added and after stirring at −70° C. for 45 min the mixture is heated at 0° C. for 1 h. Then the mixture is cooled to −70° C. and 4-methyl-6-for-mylethynyl-2-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)pyridine 0.3 g, 1 mmol) is added. After stirring for 30 min at −70° C. the reaction mixture is stirred at ambient temperature for 2 days. The mixture is quenched with water, evaporated and to the water containing residue is added ethyl acetate. The mixture is washed with diluted hydrochloric acid and with water. After drying and evaporation, the product (0.15 g) is obtained by flash chromatogy as nearly colorless crystals of mp 85° C.

Workup

temperatureis heated at 0° C. for 1 h
temperatureThen the mixture is cooled to −70° C.
stirringAfter stirring for 30 min at −70° C. the reaction mixture
stirringis stirred at ambient temperature for 2 days
customThe mixture is quenched with water
customevaporated and to the water containing residue
additionis added ethyl acetate
washThe mixture is washed with diluted hydrochloric acid and with water
customAfter drying
customevaporation

Sources & evidence

ORD record: ord-74538a4e353f4002932d5828cb086465
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872690B2

Reaction notes

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