Formaldehyde → 2-Bromo-5-[(1-methyl-3-azetidinyl)oxy]pyridine

HRID 2069727노트

반응식

HRID 2069727 반응식
F[C:2](F)(F)C(O)=O.[NH:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:14]=[CH:15][C:16]([Br:19])=[N:17][CH:18]=2)[CH2:9]1.C=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[Br:19][C:16]1[CH:15]=[CH:14][C:13]([O:12][CH:10]2[CH2:11][N:8]([CH3:2])[CH2:9]2)=[CH:18][N:17]=1

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 866450865-(Azetidin-3-yloxy)-2-bromo-pyridine trifluoro-acetic acid salt

생성물 1

HCID 594737702-Bromo-5-[(1-methyl-3-azetidinyl)oxy]pyridine수율 104.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a solution of 5-(Azetidin-3-yloxy)-2-bromo-pyridine trifluoro-acetic acid salt (0.5 g, 1.46 mmol) in dichloromethane (20 mL), add formaldehyde aqueous solution (37%, 0.58 mL, 7.29 mmol). Then add Na(OAc)3BH (0.774 g, 3.65 mmo) carefully. The reaction was stirred at room temperature under argon for 45 min. The reaction was quenched with water (30 mL), and then extracted with dichloromethane (3×20 mL). The combined organic phase was washed thoroughly with brine and water. Evaporation of solvent afford 2-Bromo-5-(1-methyl-azetidin-3-yloxy)-pyridine (0.37 g, yield 98%), which was pure enough for next step.

후처리

  1. customThe reaction was quenched with water (30 mL)
  2. extractionextracted with dichloromethane (3×20 mL)
  3. washThe combined organic phase was washed thoroughly with brine and water
  4. customEvaporation of solvent

출처 및 근거

ORD 기록
ord-9cca5c8ee4d745c3841362a2ae59b7ac
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299077B2

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