1-Tributylstannyl-3,3,3-trifluoro-1-propyne → HCID 86690334, compound

HRID 1428684Notes

Reaction equation

HRID 1428684 reaction equation
Br[C:2]1[C:3]([NH2:22])=[N:4][C:5]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:7]=1.C([Sn](CCCC)(CCCC)[C:28]#[C:29][C:30]([F:33])([F:32])[F:31])CCC>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[C:11]1([CH3:14])[CH:12]=[CH:13][C:8]([C:6]2[N:7]=[C:2]([C:28]#[C:29][C:30]([F:33])([F:32])[F:31])[C:3]([NH2:22])=[N:4][C:5]=2[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 111999321-Tributylstannyl-3,3,3-trifluoro-1-propyneHCID 86690308HCID 86690308, compound

Product 1

HCID 86690334HCID 86690334, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A solution of 3-bromo-5,6-di-p-tolylpyrazin-2-amine (Ex 1, step 3) (200 mg, 0.565 mmol) in dioxane (4 ml) bubbled with nitrogen was treated with tributyl(3,3,3-trifluoroprop-1-ynyl)stannane (238 mg, 0.621 mmol) and PdCl2(dppf)-CH2Cl2-Adduct (46.1 mg, 0.056 mmol). The resulting mixture was heated at 140° C. for 1 hour using microwave radiation. After cooling to RT, the mixture was concentrated under reduced pressure. The crude residue was dissolved in DCM and loaded onto a 25 g Silica column. Purification by chromatography on silica eluting with 0-5% EtOAc in iso-hexane afford the title compound;

Workup

  1. temperatureAfter cooling to RT
  2. concentrationthe mixture was concentrated under reduced pressure
  3. dissolutionThe crude residue was dissolved in DCM
  4. customPurification by chromatography on silica eluting with 0-5% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-9e61d58e06f3480f84a5ce672d07809c
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

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