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

HRID 2069727ノート

反応式

HRID 2069727 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9cca5c8ee4d745c3841362a2ae59b7ac
出典データセット
uspto-grants-2012_10
特許番号
US08299077B2

反応ノート

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