Tri-o-tolylphosphine → HCID 58388058, compound

HRID 2079977Notes

Reaction equation

HRID 2079977 reaction equation
[CH2:1]([O:3][CH:4]=[CH:5][Sn](CCCC)(CCCC)CCCC)[CH3:2].[NH2:19][C:20]1[N:36]=[C:35]([CH2:37][O:38][CH3:39])[CH:34]=[CH:33][C:21]=1[C:22]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29](Br)=[CH:28][CH:27]=1)=[O:23].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[F-].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN1CCCC1=O>[NH2:19][C:20]1[N:36]=[C:35]([CH2:37][O:38][CH3:39])[CH:34]=[CH:33][C:21]=1[C:22]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29](/[CH:5]=[CH:4]\[O:3][CH2:1][CH3:2])=[CH:28][CH:27]=1)=[O:23]

Participants

8

Reactant 4

HCID 80271Tri-o-tolylphosphineHCID 522689Potassium FluorideHCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)etheneHCID 23130589HCID 23130589, compound

Product 1

HCID 58388058HCID 58388058, compoundYield 40.7%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of (2-ethoxy-vinyl)-tributyl-stannane (37 mg, 0.10 mmol) synthesized according to WO02/018368, 2-amino-N-(4-bromo-benzyl)-6-methoxymethyl-nicotinamide (30 mg, 0.086 mmol) described in Preparation Example A+-23, tri-o-tolylphosphine (6.5 mg, 0.021 mmol), palladium acetate (0.96 mg, 0.0043 mmol), tetrabutylammonium chloride (24 mg, 0.086 mmol) and N-methylpyrrolidinone (1 mL) was stirred at 125° C. for 1 hour. The reaction solution was allowed to cool, an aqueous solution of potassium fluoride was added on an ice bath, the solution was filtered through Celite pad. The filtrate was partitioned with ethyl acetate. The organic layer was separated, washed with brine, then, evaporated in vacuo. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:2), and the title compound (12 mg, 0.035 mmol, 35%) was obtained as a colorless solid.

Workup

  1. customsynthesized
  2. temperatureto cool
  3. filtrationthe solution was filtered through Celite pad
  4. customThe filtrate was partitioned with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with brine
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-5d76d874caa94bca927ac67be0779772
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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