Acetic Acid → Methyl 6-(2-((dimethylamino)methyl)imidazo[1,2-a]pyridin-6-yl)-5-ethyl-2-methoxynicotinate

HRID 1481706Notes

Reaction equation

HRID 1481706 reaction equation
[CH2:1]([C:3]1[C:4]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([CH:21]=[C:22]([CH:24]=O)[N:23]=3)[CH:20]=2)=[N:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])[CH3:2].[CH3:26][NH:27][CH3:28].CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.C(Cl)Cl>[CH3:26][N:27]([CH2:24][C:22]1[N:23]=[C:18]2[CH:17]=[CH:16][C:15]([C:4]3[C:3]([CH2:1][CH3:2])=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([O:13][CH3:14])[N:5]=3)=[CH:20][N:19]2[CH:21]=1)[CH3:28]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 89423055Methyl 5-ethyl-6-(2-formylimidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinate

Product 1

HCID 71284140Methyl 6-(2-((dimethylamino)methyl)imidazo[1,2-a]pyridin-6-yl)-5-ethyl-2-methoxynicotinateYield 101.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of methyl 5-ethyl-6-(2-formylimidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinate (90 mg, 0.27 mmol) in dichloroethane (1.5 mL) was added solution of dimethylamine (2M THF, 0.20 mL, 0.40 mmol) followed by AcOH (25 μL, 0.42 mmol). After stirring at room temperature for 5 min NaBH(OAc)3 (90 mg, 0.42 mmol) was added. Reaction was stirred at room temperature ˜1.5 h and monitored by LC/MS until starting aldehyde was completely consumed. Reaction was diluted with DCM (5 mL) and then quenched with NaHCO3 (aqueous saturated, 5 mL). Product was extracted with DCM (3×5 mL). Organic phase was washed with NaCl (aqueous saturated, 10 mL) and dried over Na2SO4. Removal of the solvent afforded methyl 6-(2-((dimethylamino)methyl)imidazo[1,2-a]pyridin-6-yl)-5-ethyl-2-methoxynicotinate (100.6 mg) which was used directly in the next step. LC-MS 369.3 [M+H]+, RT 0.83 min.

Workup

  1. additionwas added
  2. customReaction
  3. customwas completely consumed
  4. customReaction
  5. customquenched with NaHCO3 (aqueous saturated, 5 mL)
  6. extractionProduct was extracted with DCM (3×5 mL)
  7. washOrganic phase was washed with NaCl (aqueous saturated, 10 mL)
  8. dry with materialdried over Na2SO4
  9. customRemoval of the solvent

Sources & evidence

ORD record
ord-64c8b635f47c416ebe066e490bea2a9e
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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