Diisopropylethylamine → HCID 86665172, compound

HRID 1893719Notes

Reaction equation

HRID 1893719 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH:12]=[C:11](I)[C:10]([C:14]([N:16]([O:18][CH3:19])[CH3:17])=[O:15])=[N:9]2)=[CH:5][CH:4]=1.[CH3:22][C:23]1[N:28]=[C:27]([O:29][C:30]2[S:31][CH:32]=[C:33](B3OC(C)(C)C(C)(C)O3)[N:34]=2)[CH:26]=[CH:25][CH:24]=1.C(N(C(C)C)C(C)C)C>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:33]3[N:34]=[C:30]([O:29][C:27]4[CH:26]=[CH:25][CH:24]=[C:23]([CH3:22])[N:28]=4)[S:31][CH:32]=3)[C:10]([C:14]([N:16]([O:18][CH3:19])[CH3:17])=[O:15])=[N:9]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 66889350HCID 66889350, compoundHCID 86665173HCID 86665173, compound

Product 1

HCID 86665172HCID 86665172, compoundYield 20.2%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
120 °C

Procedure

According to Scheme 5, Step 4: A mixture of 1-(4-methoxybenzyl)-4-iodo-N-methoxy-N-methyl-1H-pyrazole-3-carboxamide (0.59 mmol, 238 mg), 2-(6-methylpyridin-2-yloxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole (0.49 mmol, 157 mg), PdCl2(dppf) (49 μmol, 40 mg) and N-ethyl-N-isopropylpropan-2-amine (0.99 mmol, 0.17 mL) in dioxane/water (1:1, 3.3 mL) was stirred at 120° C. for 30 minutes under microwave conditions. The reaction mixture was filtered through a pad of celite and was washed with DCM. The organic phase was washed with water, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude mixture was purified by flash chromatography over silica gel using cyclohexane/EtOAc (90:10 to 70:30) as eluent to yield 1-(4-methoxybenzyl)-N-methoxy-N-methyl-4-(2-(6-methylpyridin-2-yloxy)thiazol-4-yl)-1H-pyrazole-3-carboxamide (99 μmol, 46 mg, 15%) as an oil.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washwas washed with DCM
  3. washThe organic phase was washed with water
  4. dry with materialwas dried over MgSO4
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure
  7. customThe crude mixture was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-32cfaa03963c471e9250c2202ef05bb0
Source dataset
uspto-grants-2013_08
Patent number
US08513252B2

Reaction notes

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