Piperidine → HCID 66930899, compound

HRID 1364124Notes

Reaction equation

HRID 1364124 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:17]=[C:16]3[C:10]([CH2:11][CH2:12][N:13]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:15]3)=[N:9]2)=[CH:4][CH:3]=1.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC(C)([O-])C.[Na+]>O1CCOCC1.CO.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:25]1([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH:17]=[C:16]4[C:10]([CH2:11][CH2:12][N:13]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:15]4)=[N:9]3)=[CH:4][CH:3]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

8

Reactant 4

HCID 8082PiperidineHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 66931029HCID 66931029, compound

Product 1

HCID 66930899HCID 66930899, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,1-dimethylethyl 2-(4-bromophenyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate (may be prepared as described in Description 12) (150 mg, 0.38 mmol), piperidine (76 μl, 0.76 mmol), [2′-(dicyclohexylphosphanyl)-2-biphenylyl]dimethylamine (24 mg, 0.06 mmol), tris(dibenzylideneacetone)dipalladium(0) (174 mg, 0.20 mmol), and sodium tert-butoxide (73 mg, 0.76 mmol) in dioxan (4.5 ml) was heated at 120° C. in the microwave (normal absorption) for 30 min. The reaction mixture was diluted with methanol and then purified by SCX, eluting with methanol and then 2M ammonia/methanol. The basic fractions were combined and solvent evaporated in vacuo. The crude product was purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate in hexane (0-50%) to afford the title compound. MS (ES+) m/e 397 [M+H]+.

Workup

  1. custompurified by SCX
  2. washeluting with methanol
  3. customsolvent evaporated in vacuo
  4. customThe crude product was purified by column chromatography on silica gel
  5. washeluting with a mixture of ethyl acetate in hexane (0-50%)

Sources & evidence

ORD record
ord-265b86da2eeb45498b12d43f1654486b
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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