Dimethyl Sulfoxide → Methyl 5-ethyl-6-(2-formylimidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinate

HRID 1481705Notes

Reaction equation

N1C=CC=CC=1.CS(C)=O.[CH2:11]([C:13]1[C:14]([C:25]2[CH:26]=[CH:27][C:28]3[N:29]([CH:31]=[C:32]([CH2:34][OH:35])[N:33]=3)[CH:30]=2)=[N:15][C:16]([O:23][CH3:24])=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19])[CH3:12].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:11]([C:13]1[C:14]([C:25]2[CH:26]=[CH:27][C:28]3[N:29]([CH:31]=[C:32]([CH:34]=[O:35])[N:33]=3)[CH:30]=2)=[N:15][C:16]([O:23][CH3:24])=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19])[CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

To SO3-pyr complex (0.320 g, 2.01 mmol) was added pyridine (0.16 mL, 2.02 mmol) and DMSO (0.36 mL, 5.07 mmol). Slurry was stirred at room temperature 10 min before DCM (2.0 mL) was added and mixture was cooled to 0° C. Then solution of methyl 5-ethyl-6-(2-(hydroxymethyl)imidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinate (0.346 g, 1.01 mmol), Hunig's base (0.60 mL, 3.44 mmol) and DMSO (0.36 mL, 5.07 mmol) in DCM (4.0 mL) was added dropwise. Reaction mixture was stirred at 0° C. 30 min and LC/MS showed complete consumption of starting material. DCM was removed under reduced pressure and residue was treated with H2O (10 mL). Solid which was formed was collected by filtration affording methyl 5-ethyl-6-(2-formylimidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinate (0.270 g) in 79% yield.

Workup

additionwas added
customReaction mixture
custom30 min and LC/MS
customconsumption of starting material
customDCM was removed under reduced pressure and residue
additionwas treated with H2O (10 mL)
customSolid which was formed
filtrationwas collected by filtration

Sources & evidence

ORD record: ord-02bf8e1feada4ce0a4c7224adea59084
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409905B2

Reaction notes

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