Piperidine → HCID 67466257, compound

HRID 509259Notes

Reaction equation

HRID 509259 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:14][CH2:13][C@@H:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]([F:24])([F:23])[F:22])[CH2:11]2)=[O:9])[CH:5]=[CH:4][CH:3]=1.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.CC(C)([O-])C.[Na+].[Cl-].[NH4+]>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>[N:25]1([C:2]2[N:7]=[C:6]([C:8]([N:10]3[CH2:14][CH2:13][C@@H:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:21]([F:24])([F:23])[F:22])[CH2:11]3)=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

8

Reactant 4

HCID 8082PiperidineHCID 25517Ammonium ChlorideHCID 23676156Sodium t-butoxideHCID 86692071HCID 86692071, compound

Product 1

HCID 67466257HCID 67466257, compoundYield 64.4%

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

(S)-(6-Bromopyridin-2-yl)(3-(2-(trifluoromethyl)phenyl)pyrrolidin-1-yl)methanone (60 mg, 0.150 mmol), piperidine (15 mg, 0.180 mmol), Pd2(dba)3 (3 mg, 0.003 mmol), xantphos (5 mg, 0.009 mmol), and sodium-tert-butoxide (22 mg, 0.225 mmol) were suspended in toluene (3 ml), and then stirred at 100° C. under nitrogen stream for 3 hours. A saturated aqueous ammonium chloride solution (15 ml) was added to the resulting reaction liquid, followed by extraction with MC (15 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 39 mg of pale yellow oil (64%). MS (ESI): 404 [M+H]+

Workup

  1. extractionfollowed by extraction with MC (15 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-af984e7e1bed4bee954c69ac5fc70182
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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