Water → Tert-Butyl 6-(1-methyl-1H-pyrazol-4-yl)-4-oxo-spiro[chroman-2,4'-piperidine]-1'-carboxylate

HRID 1096934Notes

Reaction equation

HRID 1096934 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:21](=[CH:22][CH:23]=1)[O:20][C:7]1([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)[CH2:6][C:5]2=[O:24].[CH3:25][N:26]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[N:27]1.O>O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].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>[CH3:25][N:26]1[CH:30]=[C:29]([C:2]2[CH:3]=[C:4]3[C:21](=[CH:22][CH:23]=2)[O:20][C:7]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:9][CH2:8]2)[CH2:6][C:5]3=[O:24])[CH:28]=[N:27]1

Participants

7

Reactant 3

HCID 962WaterHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 2794759tert-Butyl 6-bromo-4-oxospiro[chroman-2,4'-piperidine]-1'-carboxylate

Product 1

HCID 57931011Tert-Butyl 6-(1-methyl-1H-pyrazol-4-yl)-4-oxo-spiro[chroman-2,4'-piperidine]-1'-carboxylate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Tert-butyl 6-bromo-4-oxospiro-[chroman-2,4′-piperidine]-1′-carboxylate (1 g) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (682 mg) were dissolved in dioxane in a nitrogen atmosphere, and aqueous 2 M sodium carbonate solution (3.8 mL) and tetrakis(triphenylphosphine)palladium (144 mg) were added thereto, and degassed. The reaction liquid was stirred overnight at 100° C., cooled to room temperature, then water was added thereto, and filtered through Celite. The filtrate was extracted with chloroform, and the organic layer was dried with sodium sulfate. Sodium sulfate was removed through filtration, the filtrate was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate=100/0 to 0/100) to obtain the intended product as a pale yellow solid.

Workup

  1. additionwere added
  2. customdegassed
  3. customThe reaction liquid
  4. temperaturecooled to room temperature
  5. filtrationfiltered through Celite
  6. extractionThe filtrate was extracted with chloroform
  7. dry with materialthe organic layer was dried with sodium sulfate
  8. customSodium sulfate was removed through filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate=100/0 to 0/100)

Sources & evidence

ORD record
ord-74ee70213ebc4522af98dd49b1da6bd2
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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