2-(Tri-n-butylstannyl)oxazole → 5-Nitro-4-(oxazol-2-yl)thiophene-3-carbonitrile

HRID 2098152Notes

Reaction equation

HRID 2098152 reaction equation
Br[C:2]1[C:3]([C:10]#[N:11])=[CH:4][S:5][C:6]=1[N+:7]([O-:9])=[O:8].C([Sn](CCCC)(CCCC)[C:17]1[O:18][CH:19]=[CH:20][N:21]=1)CCC>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.[Cu]I>[N+:7]([C:6]1[S:5][CH:4]=[C:3]([C:10]#[N:11])[C:2]=1[C:17]1[O:18][CH:19]=[CH:20][N:21]=1)([O-:9])=[O:8]

Participants

5

Reactant 2

HCID 154861832-(Tri-n-butylstannyl)oxazoleHCID 591688104-Bromo-5-nitrothiophene-3-carbonitrile

Product 1

HCID 687544515-Nitro-4-(oxazol-2-yl)thiophene-3-carbonitrileYield 18%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

The above titled compound (34 mg, 18%) was synthesized from 4-bromo-5-nitrothiophene-3-carbonitrile (203 mg, 0.87 mmol) and 2-tributylstannyloxazole (0.27 mL, 1.29 mmol), tetrakis(triphenylphosphine)palladium(0) (103 mg, 0.089 mmol) and copper(I) iodide (16 mg, 0.084 mmol) according to methods described herein. LCMS method [4], retention time=1.62 min; MS (ESI) 222.0 (MH+).

Sources & evidence

ORD record
ord-13e230e562224ec98e982828f9616428
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

Loading…