Formic Acid → HCID 86686016, compound

HRID 2277721Notes

Reaction equation

HRID 2277721 reaction equation
[N:1]1([C:6](=[O:8])[CH3:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14](I)[CH:15]=1.C(N(CC)CC)C.C(O)=O>CN(C=O)C.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.O>[Br:9][C:10]1[CH:15]=[C:14]([CH:3]2[CH2:4][CH2:5][N:1]([C:6](=[O:8])[CH3:7])[CH2:2]2)[CH:13]=[N:12][CH:11]=1

Participants

8

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 8204093-Bromo-5-iodopyridineHCID 11446304HCID 11446304, compound

Product 1

HCID 86686016HCID 86686016, compoundYield 15%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-(2,5-dihydro-pyrrol-1-yl)-ethanone (70 mg, 0.63 mmol), 3-bromo-5-iodo-pyridine (283 mg, 1 mmol), triethyl amine (130 mg, 1.26 mmol), formic acid (41 mg, 0.88 mmol) and tetrakis(triphenylphosphine)palladium(0) (72.8 mg, 0.063 mmol) in DMF (3 mL) was stirred for 24 hours at 90° C. under nitrogen. After cooling to room temperature, the mixture was treated with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate. After removal of solvents, the residue was purified by flash chromatography to afford the title compound as yellowish oil (25 mg, 15%). MS: 269.1 (M+H+).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customAfter removal of solvents
  5. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-d5c47487d45e47ec857c09928f7089f4
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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