Sodium hydride → Ethyl 9-iodo-1-methyl-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxylate

HRID 1168517노트

반응식

HRID 1168517 반응식
[CH3:1][NH:2][C:3](=[O:6])[CH2:4][NH2:5].F[C:8]1[C:25](F)=[CH:24][C:23]([I:27])=[CH:22][C:9]=1[C:10]([C:12](=[CH:18]OCC)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:11].[H-].[Na+]>CN1C(=O)CCC1>[I:27][C:23]1[CH:22]=[C:9]2[C:10](=[O:11])[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:18][N:5]3[CH2:4][C:3](=[O:6])[N:2]([CH3:1])[C:25]([CH:24]=1)=[C:8]23

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 896752-amino-N-methylacetamideHCID 69879816Ethyl 2-(2,3-Difluoro-5-iodobenzoyl)-3-ethoxy-2-propenoate

생성물 1

HCID 12083043Ethyl 9-iodo-1-methyl-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxylate수율 60.7%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
100 °C

실험 절차

Glycine methylamide (1.0 g) is added at room temperature to a solution of ethyl 2-(2,3-difluoro-5-iodobenzoyl)-3-ethoxy-2-propenoate (Preparation 21, 2.0 g) in NMP (20 mL). Sodium hydride (400 mg, 60% dispersion in mineral oil) is added in two portions to the solution, and the solution is heated at 100° C. for 30 min. The product is partitioned between chloroform and water, the chloroform phase is concentrated and applied to a silica gel column with 1-2% methanol chloroform as the eluant. The purified fractions are triturated with ether to give 1.22 g of the title compound. Physical characteristics: M.p. 278-283° C.; 1H NMR (DMSO-d6) δ1.29, 3.63, 4.23, 5.10, 7.65, 8.09, 8.55. Anal. Found: C, 43.49; H, 3.18; N, 6.75.

후처리

  1. customThe product is partitioned between chloroform and water
  2. concentrationthe chloroform phase is concentrated
  3. customThe purified fractions are triturated with ether

출처 및 근거

ORD 기록
ord-716885f811cd43c5882c170472049ab2
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06624159B2

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