Piperidine → HCID 54591673, compound

HRID 509264Notes

Reaction equation

HRID 509264 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][C:13]([OH:20])([C:16]([F:19])([F:18])[F:17])[CH2:12][CH2:11]2)=[O:9])[CH:5]=[CH:4][CH:3]=1.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.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.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].O>[OH:20][C:13]1([C:16]([F:19])([F:18])[F:17])[CH2:14][CH2:15][N:10]([C:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[N:7]=2)=[O:9])[CH2:11][CH2:12]1

Participants

8

Reactant 4

HCID 8082PiperidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 86692074HCID 86692074, compound

Product 1

HCID 54591673HCID 54591673, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

(6-Bromopyridin-2-yl)(4-hydroxy-4-(trifluoromethyl)piperidin-1-yl)methanone (61 mg, 0.172 mmol), piperidine (0.02 ml, 0.189 mmol), Pd2(dba)3 (3 mg, 0.003 mmol), xantphos (6 mg, 0.010 mmol), and sodium-tert-butoxide (25 mg, 0.258 mmol) were suspended in toluene (1.5 ml), and then stirred at 100° C. under nitrogen stream for 2 hours. Distilled water (5 ml) was added to the resulting reaction liquid, followed by extraction with 5% MeOH/MC (10 ml×2). The organic layer was dried over anhydrous magnesium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (50% EtOAc/Hexanes), to obtain 37 mg of yellow solid (61%). MS (ESI): 358 [M+H]+

Workup

  1. extractionfollowed by extraction with 5% MeOH/MC (10 ml×2)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfollowed by filtration and concentration
  4. customthe residue thus obtained

Sources & evidence

ORD record
ord-8c5f71ae62f74235be9213e6c34522e9
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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