Potassium Carbonate → HCID 4861010, compound

HRID 230615Notes

Reaction equation

I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[F:12][C:13]([F:24])([F:23])[C:14]1[C:22]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=2[NH:16][N:15]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Cu]I>[F:24][C:13]([F:12])([F:23])[C:14]1[C:22]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=2[N:16]([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=2)[N:15]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of methyl 4-iodobenzoate (1.40 g, 5.34 mmol), 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (1.22 g, 6.42 mmol), copper (I) iodide (1 mol %, 10 mg, 0.05 mmol), trans-1,2-diaminocyclohexane (10 mol %, 62 mg, 0.54 mmol) and potassium carbonate (1.56 g, 11.3 mmol) in 1,4-dioxane (8 ml) was stirred at 180° C. in a microwave reactor for 45 minutes, then fresh copper (I) iodide (1 mol %, 10 mg, 0.05 mmol) and trans-1,2-diaminocyclohexane (10 mol %, 62 mg, 0.54 mmol) were added and the reaction stirred at 180° C. in a microwave reactor for 1 h 45 minutes. The reaction mix was cooled and added to a 50 g pre-packed silica column which was then eluted from 0-50% ethyl acetate in petroleum ether to give a crop of the title compound as a brown oil (630 mg, 36%).

Workup

stirringthe reaction stirred at 180° C. in a microwave reactor for 1 h 45 minutes
additionThe reaction mix
temperaturewas cooled
additionadded to a 50 g pre-packed silica column which
washwas then eluted from 0-50% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-8ebfbac336454333aedd14bc8465d5d2
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566735B2

Reaction notes

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