N,N-Dimethylglycine → Methyl 3-(6-aminopyridin-3-yloxy)benzoate

HRID 1684936

반응식

HRID 1684936 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[OH:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14].CN(C)CC(O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.[Cu]I>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([O:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])=[CH:3][CH:4]=1

참가 물질

7

반응물 4

HCID 673N,N-DimethylglycineHCID 10796Cesium carbonateHCID 706222-Amino-5-bromopyridineHCID 88068Methyl 3-Hydroxybenzoate

생성물 1

HCID 67263263Methyl 3-(6-aminopyridin-3-yloxy)benzoate수율 51.2%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

A procedure described by D. Ma and Q. Cai (Org. Lett. 3799, 2003) was followed. To a solution of 5-bromopyridin-2-amine (346 mg, 2 mmol) in dioxane (10 mL) were added methyl 3-hydroxybenzoate (400 mg, 2.6 mmol), CuI (50 mg), N,N-dimethylglycine (60 mg) and Cs2CO3 (1.0 g). The resulting mixture was heated to 120° C. for 5 h, then cooled and partitioned between water and dichloromethane. The organic layer was separated, dried, and concentrated. The residue was purified by silica gel column eluting with ethyl acetate in dichloromethane (1:1) to obtain methyl 3-(6-aminopyridin-3-yloxy)benzoate (250 mg, 50%) as an oil. LC/MS; (M+H)+=245.

후처리

  1. temperaturecooled
  2. custompartitioned between water and dichloromethane
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column
  7. washeluting with ethyl acetate in dichloromethane (1:1)

출처 및 근거

ORD 기록
ord-1a2cae8af1bd4feda962544efec2b2ed
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148361B2

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