Triethylamine → 1-(4-{4-[(2-Methoxyphenyl)ethynyl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

HRID 549970Notes

Reaction equation

HRID 549970 reaction equation
C(N(CC)CC)C.[C:8]([C:10]1[N:11]=[C:12]([CH:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:33])[CH2:22][N:23]3[C:27]([CH3:28])=[CH:26][C:25]([C:29]([F:32])([F:31])[F:30])=[N:24]3)[CH2:17][CH2:16]2)[S:13][CH:14]=1)#[CH:9].I[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[O:41][CH3:42]>CN(C)C=O.O.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.[Cu]I>[CH3:42][O:41][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[C:9]#[C:8][C:10]1[N:11]=[C:12]([CH:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:33])[CH2:22][N:23]3[C:27]([CH3:28])=[CH:26][C:25]([C:29]([F:30])([F:32])[F:31])=[N:24]3)[CH2:17][CH2:16]2)[S:13][CH:14]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 68257o-IodoanisoleHCID 866420471-[4-(4-Ethynyl-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

Product 1

HCID 671563421-(4-{4-[(2-Methoxyphenyl)ethynyl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (25 mg), copper(I) iodide (7 mg) and triethylamine (48 mg) are added to a solution of 1-[4-(4-ethynyl-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (I-86, 150 mg) and 1-iodo-2-methoxybenzene (101 mg) in degassed N,N-dimethylformamide (1.5 ml). After 2 hours of stirring at 85° C., the reaction mixture is then diluted with water and extracted with ethyl acetate. The organic extracts are dried over sodium sulphate and concentrated under reduced pressure. After chromatographic purification, this gives 1-(4-{4-[(2-methoxyphenyl)ethynyl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (100 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts are dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customAfter chromatographic purification

Sources & evidence

ORD record
ord-0fee0cd8f6514434bf9cf9a56dd52971
Source dataset
uspto-grants-2011_05
Patent number
US07943774B2

Reaction notes

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