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

HRID 1921308Notes

Reaction equation

Br[C:2]1[S: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[S: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

Conditions

Temperature: 90 °C

Procedure

To a mixture of 5-bromothiophene-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, 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)thiophene-2-carbaldehyde (1.2 g, 103% yield).

Workup

temperatureThe reaction is cooled
washwashed with water
customThe organic layer is separated
customdried
filtrationfiltered
concentrationconcentrated
customThe residue is purified by flash chromatography
washeluting with heptane-30% ethyl acetate

Sources & evidence

ORD record: ord-1830d4710f894fcfbb63abaa4c9aba6a
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173682B2

Reaction notes

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