Potassium Carbonate → Ethyl {4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]phenyl}acetate

HRID 230618Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1)[CH3:2].[F:14][C:15]([F:26])([F:25])[C:16]1[C:24]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=2[NH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>C1(C)C=CC=CC=1.[Cu]I.CN[C@@H]1CCCC[C@H]1NC>[F:26][C:15]([F:14])([F:25])[C:16]1[C:24]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=2[N:18]([C:9]2[CH:10]=[CH:11][C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:13])=[CH:7][CH:8]=2)[N:17]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of ethyl-4-bromophenylacetate (875 mg, 3.60 mmol), 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (570 mg, 3.00 mmol), potassium carbonate (842 mg, 6.10 mmol), copper (I) iodide (5 mol %, 29 mg, 0.15 mmol), and (1R,2R)-N,N′-dimethyl-1,2-cyclohexanediamine (20 mol %, 85 mg, 0.60 mmol) in toluene (2 ml) was stirred under an atmosphere of argon at 130° C. in a microwave reactor for 1 h. Further copper (I) iodide (10 mg, 0.05 mmol), and (1R,2R)-N,N′-dimethyl-1,2-cyclohexanediamine (30 mg, 0.21 mmol) was added and heating continued at 130° C. for a total of 4 h. The reaction mix was cooled and added to a 20 g pre-packed silica column and eluted with 0-20% ethyl acetate in petroleum ether to give the title compound as a brown oil (0.92 g, 87%).

Workup

temperatureheating
customcontinued at 130° C. for a total of 4 h
additionThe reaction mix
temperaturewas cooled
additionadded to a 20 g pre-packed silica column
washeluted with 0-20% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-b76a493bfe714ba6bec24eb1bde4e460
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566735B2

Reaction notes

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