1,4-Dioxane → HCID 68755813, compound

HRID 1519929Notes

Reaction equation

HRID 1519929 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[S:21][CH:20]=[N:19][CH:18]=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.[Cu](I)I.CN(C=O)C>[N+:7]([C:6]1[S:5][CH:4]=[C:3]([C:10]#[N:11])[C:2]=1[C:17]1[S:21][CH:20]=[N:19][CH:18]=1)([O-:9])=[O:8]

Participants

7

Reactant 3

HCID 312751,4-DioxaneHCID 27632575-(Tributylstannyl)-1,3-thiazoleHCID 591688104-Bromo-5-nitrothiophene-3-carbonitrile

Product 1

HCID 68755813HCID 68755813, compoundYield 61.4%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A microwave vial equipped with a stir bar was added 4-bromo-5-nitrothiophene-3-carbonitrile (0.24 g, 1.05 mmole) and tetrakis(triphenylphosphine)palladium (0) (0.14 g, 0.12 mmol), copper iodide (0.028 g, 0.15 mmol) and then purged with N2 (g) inlet prior to addition of 5-(tributylstannyl)thiazole (0.63 g, 1.67 mmol), dioxane (2.3 mL) and few drops of DMF. The reaction mixture was heated at 110° C. for 30 min and then concentrated under reduced pressure. Purification by flash chromatography (silica, 40:60 ethyl acetate/hexane) gave 5-nitro-4-(thiazol-5-yl)thiophene-3-carbonitrile (153 mgs, 61%) Retention time (min)=1.715, method [4], MS(ESI) 238.0 (M+H).

Workup

  1. customA microwave vial equipped with a stir bar
  2. custompurged with N2 (g) inlet
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography (silica, 40:60 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-26f0ffc12a6743ef83e7ec5362014127
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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