Water → HCID 59595975, compound

HRID 2264187Notes

Reaction equation

HRID 2264187 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:18]1[O:19][CH:20]=[CH:21][N:22]=1)CCC.O1CCOCC1.O>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.C(OCC)(=O)C>[CH3:9][O:8][C:6]1[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=[C:2]([C:18]2[O:19][CH:20]=[CH:21][N:22]=2)[N:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 107977036-Chloro-2-methoxy-3-nitropyridineHCID 154861832-(Tri-n-butylstannyl)oxazole

Product 1

HCID 59595975HCID 59595975, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

An oven-dried resealable Schlenk tube was charged with 6-chloro-2-methoxy-3-nitropyridine (0.50 g, 2.6 mmol), 2-tributylstannanyloxazole (1.20 g, 3.4 mmol) and 1,4-dioxane (10 mL) and then subjected to several cycles of evacuation-backfilling with argon. Tetrakis(triphenylphosphine)palladium (0.18 g, 0.16 mmol) was then added and, after three new cycles of evacuation-backfilling with argon, the Schlenk tube was sealed and the mixture was stirred and heated in an oil bath to 110° C. After stirring overnight, water and ethyl acetate were added and the organic layer was washed with water, dried (MgSO4) and evaporated. The residue was purified by flash chromatography (2:1 hexanes/ethyl acetate) to give the title compound (0.38 g, 67%) as a yellow solid.

Workup

  1. customafter three new cycles of evacuation-backfilling with argon, the Schlenk tube was sealed
  2. stirringAfter stirring overnight
  3. washthe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography (2:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-699769929302401a882e63a5a68e2fa8
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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