Pyridine → Methyl 4-(3-methyl-6-{[6-(1-methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4'-piperidin]-1'-yl]carbonyl}-1H-indazol-1-yl)benzoate

HRID 38465

Reaction equation

HRID 38465 reaction equation
N1C=CC=CC=1.[CH3:7][C:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([N:19]3[CH2:24][CH2:23][C:22]4([CH2:33][C:32](=[O:34])[C:31]5[C:26](=[CH:27][CH:28]=[C:29]([C:35]6[CH:36]=[N:37][N:38]([CH3:40])[CH:39]=6)[CH:30]=5)[O:25]4)[CH2:21][CH2:20]3)=[O:18])=[CH:14][CH:15]=2)[NH:10][N:9]=1.[CH3:41][O:42][C:43]([C:45]1[CH:50]=[CH:49][C:48](B(O)O)=[CH:47][CH:46]=1)=[O:44]>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:7][C:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([N:19]3[CH2:20][CH2:21][C:22]4([CH2:33][C:32](=[O:34])[C:31]5[C:26](=[CH:27][CH:28]=[C:29]([C:35]6[CH:36]=[N:37][N:38]([CH3:40])[CH:39]=6)[CH:30]=5)[O:25]4)[CH2:23][CH2:24]3)=[O:18])=[CH:14][CH:15]=2)[N:10]([C:48]2[CH:49]=[CH:50][C:45]([C:43]([O:42][CH3:41])=[O:44])=[CH:46][CH:47]=2)[N:9]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 27343694-Methoxycarbonylphenylboronic acidHCID 178434311HCID 178434311, compound

Product 1

HCID 58208718Methyl 4-(3-methyl-6-{[6-(1-methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4'-piperidin]-1'-yl]carbonyl}-1H-indazol-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.080 ml, 0.988 mmol) was added to a stirred mixture of 1′-[(3-methyl-1H-indazol-6-yl)carbonyl]-6-(1-methyl-1H-pyrazol-4-yl)spiro[chroman-2,4′-piperidin]-4-one (150 mg, 0.329 mmol), [4-(methoxycarbonyl)phenyl]boronic acid (119 mg, 0.659 mmol), Cu(OAc)2 (90 mg, 0.494 mmol) in CH2Cl2 (1.5 ml) and the mixture was stirred at room temperature overnight. The mixture was filtered and the solvent was evaporated under reduced pressure. The residue was purified by silicagel column chromatography (hexane/EtOAc) to give intended compound as colorless oil.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silicagel column chromatography (hexane/EtOAc)
  4. customto give

Sources & evidence

ORD record
ord-237c1c2aa4ad44cba971796595c3eaf1
Source dataset
uspto-grants-2013_09
Patent number
US08524730B2

Linked notes

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