Piperidine → HCID 67467060, compound

HRID 509245Notes

Reaction equation

HRID 509245 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:9])[CH:5]=[CH:4][CH:3]=1.[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[CH:11]1([NH:10][C:8](=[O:9])[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[N:7]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 3

HCID 8082PiperidineHCID 14398805HCID 14398805, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 67467060HCID 67467060, compoundYield 91.5%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

6-bromo-N-cyclohexylpicolinamide (55 mg, 0.194 mmol), piperidine (18 mg, 0.213 mmol), Pd2(dba)3 (3.5 mg, 0.00388 mmol), xantphos (6.7 mg, 0.0116 mmol), and sodium-tert-butoxide (27.4 mg, 0.285 mmol) were suspended in toluene (3 ml), and then stirred at 100° C. under nitrogen stream for 3 hours. The resulting reaction liquid was concentrated under reduced pressure, and then the residue thus obtained was subjected to MPLC (30% EtOAc/Hexanes), to obtain 51 mg of pale yellow oil (83%). MS (ESI): 288 [M+H]+

Workup

  1. customThe resulting reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue thus obtained

Sources & evidence

ORD record
ord-7bb465b790634afbba6f6d7e2da9559f
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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