2-(Tributylstannyl)pyridine → HCID 117856975, compound

HRID 1750330Notes

Reaction equation

HRID 1750330 reaction equation
I[C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:12][C:13]([F:16])([F:15])[F:14])[CH:7]=[N:6][C:5]=2[N:4]([CH3:17])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:17][N:4]1[C:5]2[N:6]=[CH:7][N:8]([CH2:12][C:13]([F:16])([F:15])[F:14])[C:9](=[O:11])[C:10]=2[C:2]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[CH:3]1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 89810825HCID 89810825, compound

Product 1

HCID 117856975HCID 117856975, compoundYield 21.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-iodo-7-methyl-3-(2,2,2-trifluoroethyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (2 g, 5.60 mmol) and 2-(tributylstannyl)pyridine (2.2 ml, 6.79 mmol) in toluene (20 ml) was degassed. To the mixture was added tetrakis(triphenylphosphine)palladium(0) (0.324 g, 0.280 mmol). The resulting mixture was heated at 90° C. for 18 h. The reaction mixture was cooled and placed directly onto a silica column and purified by flash chromatography (0-100% ethyl acetate/cyclohexane) to give the title compound (0.37 g, 21%). LCMS RT=0.63 min, M+H+=309.1

Workup

  1. customwas degassed
  2. temperatureThe reaction mixture was cooled
  3. custompurified by flash chromatography (0-100% ethyl acetate/cyclohexane)

Sources & evidence

ORD record
ord-52f37b41175f42df9ebebb10af61131c
Source dataset
uspto-grants-2015_10
Patent number
US09156853B2

Reaction notes

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