Potassium Phosphate, Tribasic → HCID 66891214, compound

HRID 1897938Notes

Reaction equation

HRID 1897938 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18](Br)[N:17]=2)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][Si:24]([CH3:36])([CH3:35])[CH2:25][CH2:26][O:27][CH2:28][N:29]1[CH:33]=[CH:32][C:31]([NH2:34])=[N:30]1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(Cl)(Cl)Cl.O1CCOCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:34][C:31]3[CH:32]=[CH:33][N:29]([CH2:28][O:27][CH2:26][CH2:25][Si:24]([CH3:36])([CH3:35])[CH3:23])[N:30]=3)[N:17]=2)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 57562604HCID 57562604, compoundHCID 58097102HCID 58097102, compound

Product 1

HCID 66891214HCID 66891214, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 469 mg of 1-benzyl-4-((6-bromopyridin-2-yl)methyl)piperidin-4-ol, 332 mg of 1((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-amine (WO2006/046734, page 132, Reference 2), 150 mg of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 134 mg of tris(dibenzylideneacetone)dipalladium(0)-chloroform complex, 827 mg of potassium phosphate and 10 ml of 1,4-dioxane was stirred at 100° C. overnight, followed by cooling to room temperature. The reaction mixture was diluted with chloroform. An insoluble matter was filtered off using Celite, washed with chloroform, and the filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=10/1) to give the title compound as a pale yellow oil.

Workup

  1. temperatureby cooling to room temperature
  2. filtrationAn insoluble matter was filtered off
  3. washwashed with chloroform
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe resulting residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-9fbb558a5d75444cb9cba4c4e0764c79
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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