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

HRID 1481706
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HRID 1481706 반응식
[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]
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참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
HCID 63651,1-Dichloroethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-64c8b635f47c416ebe066e490bea2a9e
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09409905B2

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