2-(Tri-n-butylstannyl)thiophene → HCID 86674313, compound

HRID 509613Notes

Reaction equation

HRID 509613 reaction equation
Br[C:2]1[N:3]=[C:4]([CH:8]=[O:9])[N:5]([CH3:7])[CH:6]=1.C([Sn](CCCC)(CCCC)[C:15]1[S:16][CH:17]=[CH:18][CH:19]=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.CN(C=O)C>[CH3:7][N:5]1[CH:6]=[C:2]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)[N:3]=[C:4]1[CH:8]=[O:9]

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 127422794-broMo-1-Methyl-1H-iMidazole-2-carbaldehyde

Product 1

HCID 86674313HCID 86674313, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

A glass vial was charged with 4-bromo-1-methyl-1H-imidazole-2-carbaldehyde (1420 mg, 7.5 mmol), tributyl-(2-thienyl)-stannane (3.50 g, 9.38 mmol), DMF (15 mL) and the slurry was deoxygenated by bubbling argon through then tetrakis(triphenylphosphine)palladium(0) (216 mg, 0.1875 mmol) was added and the vessel sealed and heated in a microwave reactor at 160° C. for 30 minutes. The volatiles were removed in vacuo then EtOAc (50 mL) was added followed by saturated sodium bicarbonate solution (25 mL). The organic layer was separated and the aqueous extracted with EtOAc (50 mL). The combined extracts were dried over Na2SO4, filtered and the volatiles removed in vacuo. The residue was purified by column chromatography on silica gel (Gradient: n-heptane/EtOAc=4/1 to EtOAc 100%) to yield the title compound (730 mg, 51%) as a yellow solid. 1H NMR (500 MHz, CDCl3): δ 9.72 (s, 1H), 7.99 (s, 1H), 7.49-7.47 (m, 1H), 7.40-7.38 (m, 1H), 7.12-7.08 (m, 1H), 3.95 (s, 3H).

Workup

  1. customthe slurry was deoxygenated
  2. additionwas added
  3. customthe vessel sealed
  4. customThe volatiles were removed in vacuo
  5. additionEtOAc (50 mL) was added
  6. customThe organic layer was separated
  7. extractionthe aqueous extracted with EtOAc (50 mL)
  8. dry with materialThe combined extracts were dried over Na2SO4
  9. filtrationfiltered
  10. customthe volatiles removed in vacuo
  11. customThe residue was purified by column chromatography on silica gel (Gradient: n-heptane/EtOAc=4/1 to EtOAc 100%)

Sources & evidence

ORD record
ord-5fd1c220104041f4b6b71cf01b60b38f
Source dataset
uspto-grants-2015_08
Patent number
US09096589B2

Reaction notes

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