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

HRID 1684936

反応式

HRID 1684936 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1a2cae8af1bd4feda962544efec2b2ed
出典データセット
uspto-grants-2012_04
特許番号
US08148361B2

関連ノート

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