2-(Tributylstannyl)pyrazine → HCID 57948928, compound

HRID 1992280Notes

Reaction equation

HRID 1992280 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[S:9][CH2:10][CH2:11][C@:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17](Br)[CH:16]=2)([CH3:14])[N:13]=1)([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:29]1[CH:34]=[N:33][CH:32]=[CH:31][N:30]=1)CCC>O1CCOCC1.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>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C@:12]2([CH3:14])[CH2:11][CH2:10][S:9][C:8]([NH:7][C:6](=[O:23])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[N:13]2)=[CH:16][C:17]=1[C:29]1[CH:34]=[N:33][CH:32]=[CH:31][N:30]=1

Participants

5

Reactant 2

HCID 27373162-(Tributylstannyl)pyrazineHCID 68539143HCID 68539143, compound

Product 1

HCID 57948928HCID 57948928, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of (S)-[4-(3-bromo-4-fluoro-phenyl)-4-methyl-5,6-dihydro-4H-[1,3]thiazin-2-yl]-carbamic acid tert-butyl ester (100 mg, 250 μmoles, 1 equiv), tetrakis(triphenylphosphine)palladium (14 mg, 12.40 μmoles, 0.05 equiv) and 2-tributylstannylpyrazine (96 mg, 250 μmoles, 1 equiv) in dioxane (3 mL) is irradiated in a laboratory-grade microwave to a temperature of 130° C. and held for 20 minutes. The solvent is removed under reduced pressure and the residue is purified by silica gel chromatography eluting with a linear gradient of hexane to hexane:ethyl acetate (1:4) ramp 20 min to give the title compound (14% yield, 90% purity as determined by LCMS): MS (m/z): 403 (M+1).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue is purified by silica gel chromatography
  3. washeluting with a linear gradient of hexane to hexane:ethyl acetate (1:4) ramp 20 min

Sources & evidence

ORD record
ord-52a103a2196940e89453ed9ccffccdff
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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