Triethylamine → HCID 57441164, compound

HRID 1517109Notes

Reaction equation

HRID 1517109 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[O:9])[C:5]([CH3:21])=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1.CCN(CC)CC.[C]=O.CO.C[CH2:44][O:45][C:46](C)=[O:47]>[Pd](Cl)Cl>[CH3:44][O:45][C:46]([C:2]1[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)=[CH:4][C:5]([CH3:21])=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[O:9])[N:7]=1)=[O:47]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 21584119Ethylacetate methanolHCID 44547211[6-Chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanoneHCID 178418416HCID 178418416, compound

Product 1

HCID 57441164HCID 57441164, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 24290Palladium ChlorideCatalyst

Procedure

To a degassed solution of 7.00 g (15.5 mmol) of [6-chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 3) in 180 ml of MeOH/EtOAc 1:1 were added 0.70 g (0.86 mmol) of (1,1′-bis-diphenylphosphino)-ferrocene)palladium-(II)dichloride (1:1 complex with CH2Cl2) and 5.4 ml=3.92 g (38.7 mmol) of Et3N. This reaction mixture was stirred in an autoclave and in a carbon monoxide atmosphere at 130° C./70 bar for 30 hours. Then, it was evaporated, the residue dissolved in H2O/EtOAc and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1) to give 4.61 g (63%) of the title compound as light brown foam. MS: 476.2 (MH+).

Workup

  1. customThen, it was evaporated
  2. dissolutionthe residue dissolved in H2O/EtOAc
  3. extractionextracted twice with EtOAc
  4. washthe organic phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1)

Sources & evidence

ORD record
ord-ab7ba4598b80476cbb205b1adce528d6
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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