Heptane → HCID 11673096, compound

HRID 1921379Notes

Reaction equation

HRID 1921379 reaction equation
CC1(C)C(C)(C)C=[N:5][C:4](B2OCCO2)=C1.[C:16](=[O:19])([O-])[O-].[K+].[K+].Br[C:23]1[S:24][CH:25]=[CH:26][CH:27]=1.[CH3:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>CN(C)C=O.C(OCC)(=O)C.ClCCl.[Pd].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:29]([C:30]1[C:4]([O:19][CH3:16])=[N:5][C:33]([CH3:34])=[C:32]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[CH:31]=1)[CH3:28]

Participants

8

Reactant 4

HCID 8900HeptaneHCID 11430Potassium CarbonateHCID 138512-BromothiopheneHCID 866103514,4,5,5-Tetramethyl-[1,3,2-dioxaborolan-2-yl)pyridine

Product 1

HCID 11673096HCID 11673096, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 178478476HCID 178478476, compoundCatalystHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
107.5 °C

Procedure

Under a nitrogen atmosphere, a three neck round bottom flask is charged with 3-ethyl-2-methoxy-6-methyl-5-(4,4,5,5-tetramethyl-[1,3,2-dioxaborolan-2-yl)pyridine (7.8 g, 28.14 mmol) as prepared above, potassium carbonate (9.72 g, 70.33 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]-palladium dichloromethane (1.23 mg, 1.68 mmol) followed by anhyd dimethylformamide (100 mL). To this is added a solution of 2-bromothiophene (9.2 g, 56.44 mmol) in dimethylformamide (10 mL) and the resulting mixture is heated to 105-110° C. for 16 hr. The reaction is cooled, diluted with ethyl acetate and washed with water, with brine, dried (sodium sulfate), filtered and concentrated. The residue is purified by flash chromatography eluting with heptane, then heptane-5% ethyl acetate to afford 3-ethyl-2-methoxy-6-methyl-5-(thiophen-2-yl)pyridine as a yellow oil (94% yield).

Workup

  1. temperatureThe reaction is cooled
  2. washwashed with water, with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography
  7. washeluting with heptane

Sources & evidence

ORD record
ord-b82d2388aee24862b1c66dc077e0cfd6
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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