Cesium carbonate → HCID 86706557, compound

HRID 1486739Notes

Reaction equation

HRID 1486739 reaction equation
[CH:1]1([NH:7][C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19](Cl)[CH:18]=3)[CH2:12][CH2:11]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([NH2:31])=[O:30])=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.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]>[CH:1]1([NH:7][C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:31][C:29](=[O:30])[C:28]4[CH:32]=[CH:33][C:25]([F:24])=[CH:26][CH:27]=4)[CH:18]=3)[CH2:12][CH2:11]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 715724-FluorobenzamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86706558HCID 86706558, compound

Product 1

HCID 86706557HCID 86706557, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

A suspension of 1-(2-chloro-pyridin-4-ylmethyl)-piperidine-4-carboxylic acid cyclohexylamide (50 mg, 0.15 mol), 4-fluoro-benzamide (20 mg, 0.15 mmol) and Cs2CO3 (5 mg, 0.16 mmol) in degassed dioxane (3 mL) is treated with 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (17 mg, 0.030 mmol) and tris(dibenzylideneacetone)dipalladium(0) (6.8 mg, 0.007 mmol). The reaction mixture is heated overnight at 100° C. The mixture is filtered, evaporated, dissolved in MeCN (1 mL) and purified by prep HPLC E. The product is dissolved in 2 ml HCl 1.25 N in MeOH and re-evaporated at HV, delivering the title compound hydrochloride as a slightly yellow powder, LC-MS A: tR=0.67 min; [M+H]+=439.3.

Workup

  1. filtrationThe mixture is filtered
  2. customevaporated
  3. dissolutiondissolved in MeCN (1 mL)
  4. custompurified by prep HPLC E
  5. dissolutionThe product is dissolved in 2 ml HCl 1.25 N in MeOH
  6. customre-evaporated at HV

Sources & evidence

ORD record
ord-0a59ee650b4f4f46b9319c72796a62c2
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

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