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

HRID 1481705
Notes
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Reaction equation

HRID 1481705 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 1049PyridineHCID 81531DiisopropylethylamineHCID 71284396Methyl 5-ethyl-6-(2-(hydroxymethyl)imidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinate

Product 1

HCID 89423055Methyl 5-ethyl-6-(2-formylimidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinateYield 79%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent2×

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

  1. additionwas added
  2. customReaction mixture
  3. custom30 min and LC/MS
  4. customconsumption of starting material
  5. customDCM was removed under reduced pressure and residue
  6. additionwas treated with H2O (10 mL)
  7. customSolid which was formed
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes