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

HRID 38476
Notes
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Reaction equation

HRID 38476 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 178418397
HCID 178418397, compound
Catalyst
HCID 10340Sodium CarbonateSolvent
HCID 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 2M Na2CO3 (10 ml) 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/EtOAc) to obtain the intended compound 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/EtOAc)

Sources & evidence

ORD record
ord-67eb52c178e84a9ea08b3ca34d24cc0a
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524730B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes