Dimethylformamide → 5-(5-Ethyl-6-methoxy-2-methylpyridin-3-yl)furan-2-carbaldehyde

HRID 1921310Notes

Reaction equation

HRID 1921310 reaction equation
Br[C:2]1[O:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.C[C:10]1([CH3:23])[C:15]([CH3:17])(C)[CH:14]=[N:13][C:12](B2OCCO2)=[CH:11]1.[C:24](=[O:27])([O-])[O-].[K+].[K+].CN(C)[CH:32]=[O:33]>O.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]>[CH2:10]([C:15]1[CH:17]=[C:7]([C:5]2[O:6][C:2]([CH:24]=[O:27])=[CH:3][CH:4]=2)[C:12]([CH3:11])=[N:13][C:14]=1[O:33][CH3:32])[CH3:23]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 6003285-Bromofuran-2-carbaldehydeHCID 866103514,4,5,5-Tetramethyl-[1,3,2-dioxaborolan-2-yl)pyridine

Product 1

HCID 116228885-(5-Ethyl-6-methoxy-2-methylpyridin-3-yl)furan-2-carbaldehydeYield 103%

Reagents, catalysts & solvents 2

HCID 178478476HCID 178478476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 5-bromofuran-2-carbaldehyde (1.25 g, 7.14 mmol), 3-ethyl-2-methoxy-6-methyl-5-(4,4,5,5-tetramethyl-[1,3,2-dioxaborolan-2-yl)pyridine (1.32 g, 4.76 mmol), prepared in accordance with one of the procedures of Step 1, PREPARATION 2, potassium carbonate (2.63 g, 7.14 mmol) and dimethylformamide (30 mL) under a nitrogen atmosphere is added dichloro[1,1′-bis(diphenylphosphino)ferrocene]-palladium dichloromethane adduct (0.2 g, 6 mol %) and the mixture is stirred at 90° C. for 2 hr. The reaction is cooled, diluted with water and washed with water. The organic layer is separated, dried, filtered and concentrated. The residue is purified by flash chromatography eluting with heptane-30% ethyl acetate to afford 5-(5-ethyl-6-methoxy-2-methylpyridin-3-yl)furan-2-carbaldehyde (1.2 g, 103% yield). MS: m/e=246 (M+H). 1H-NMR (CDCl3, δ ppm) 9.64 (s, 1H), 7.79 (s, 1H), 7.33 (d, 1H, J=3.8 Hz), 6.67 (d, 1H, J=3.8 Hz); 3.99 (s, 3H); 2.64 (s, 3H); 2.61 (q, 2H, J=7.6 Hz), 1.21 (t, 3H, J=7.6 Hz).

Workup

  1. temperatureThe reaction is cooled
  2. washwashed with water
  3. customThe organic layer is separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by flash chromatography
  8. washeluting with heptane-30% ethyl acetate

Sources & evidence

ORD record
ord-73fab38bd5af43fdb36b09473b8065c0
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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