Potassium Carbonate → HCID 86724258, compound

HRID 873716Notes

Reaction equation

HRID 873716 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[N:6][NH:7][CH:8]=1.Br[C:10]1[CH:11]=[C:12]2[C:20](=[CH:21][CH:22]=1)[O:19][C:18]1([CH2:25][CH2:24][CH2:23]1)[C:14]1([CH2:17][O:16][CH2:15]1)[C:13]2=[O:26].CN[C@@H]1CCCC[C@H]1NC.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1.[Cu]I>[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[N:6][N:7]([C:10]2[CH:11]=[C:12]3[C:20](=[CH:21][CH:22]=2)[O:19][C:18]2([CH2:25][CH2:24][CH2:23]2)[C:14]2([CH2:17][O:16][CH2:15]2)[C:13]3=[O:26])[CH:8]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 230808594-(Methoxymethyl)-1H-pyrazoleHCID 86724259HCID 86724259, compound

Product 1

HCID 86724258HCID 86724258, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 4-(methoxymethyl)-1H-pyrazole (145 mg, 1.29 mmol), 6′-bromo-4′H-dispiro[cyclobutane-1,2′-chromene-3′,3″-oxetan]-4′-one (200 mg, 0.647 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (74 mg, 0.52 mmol) and K2CO3 (268 mg, 1.94 mmol) in NMP (2 mL) was purged with argon. To the mixture was added CuI (49 mg, 0.26 mmol), and the mixture was sealed and stirred for 1 hour at 150° C. and 0.5 hours at 170° C. under a microwave irradiation. The mixture was partitioned between EtOAc and saturated aqueous NH4Cl. The organic layer was washed with water (two times) and brine, dried over MgSO4, filtered, and the filtrate was evaporated. Silicagel column chromatography (EtOAc-hexane, a linear gradient of EtOAc from 0 to 45%) afforded 6′-[4-(methoxymethyl)-1H-pyrazol-1-yl]-4′H-dispiro[cyclobutane-1,2′-chromene-3′,3″-oxetan]-4′-one (97 mg).

Workup

  1. customwas purged with argon
  2. customthe mixture was sealed
  3. customThe mixture was partitioned between EtOAc and saturated aqueous NH4Cl
  4. washThe organic layer was washed with water (two times) and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-bf4b13b681f74d2ca0209d4d282970ad
Source dataset
uspto-grants-2015_03
Patent number
US08975415B2

Reaction notes

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