Water → N-(3-Fluoro-4-pyridinyl)-N-(3-methyl-1H-indol-1-yl)glycine ethyl ester

HRID 1197623ノート

反応式

HRID 1197623 の反応式
[H-].[Na+].[F:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[NH:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH3:20])=[CH:12]1.Cl[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].O>CN(C)C=O>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][N:10]([C:9]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[F:3])[N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH3:20])=[CH:12]1)[CH3:27]

参加物

6

反応物 4

HCID 962WaterHCID 7751Ethyl chloroacetateHCID 24758Sodium hydrideHCID 9942843N-(3-Fluoro-4-pyridinyl)-3-methyl-1H-indol-1-amine

生成物 1

HCID 15818612N-(3-Fluoro-4-pyridinyl)-N-(3-methyl-1H-indol-1-yl)glycine ethyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
-20 °C

実験手順

To a suspension of NaH (60% in oil, 1.48 g) in 10 ml of dimethylformamide (DMF) at ice bath temperature was added dropwise a solution of N-(3-fluoro-4-pyridinyl)-3-methyl-1H-indol-1-amine (8.5 g) in 40 ml of DMF, when addition was complete, the mixture was stirred for 15 minutes at ice bath temperature, and then cooled to -20° C. Ethyl chloroacetate (3.95 ml) was added dropwise in 10 ml of DMF. The mixture was stirred at -20° C. for one hour. The mixture was then poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried (sat. NaCl, anhy. MgSO4). After filtering, the solvent was evaporated to yield an oil (12.2 g) which was eluted with 10% ethyl acetate/DCM on a silica gel column via HPLC. The desired fractions were evaporated to yield 6.9 g of a solid, m.p. 105°-108° C.

後処理

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at -20° C. for one hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (sat. NaCl
  6. filtrationAfter filtering
  7. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-bd7e5cfd453e498d9167140d5811aadc
出典データセット
uspto-grants-1994_01
特許番号
US05276156

反応ノート

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