Methanesulfonyl chloride → 4-Chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile-7-oxide

HRID 60248노트

반응식

HRID 60248 반응식
[CH3:1][Si:2]([CH3:25])([CH3:24])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2[CH:12]=[N+:13]([O-:18])[C:14]([C:16]#[N:17])=[CH:15][C:10]=2[C:9]2=[CH:19][CH:20]=[CH:21][N+:22]([O-])=[C:8]12.CS([Cl:30])(=O)=O>CN(C)C=O.C(OCC)(=O)C.O>[Cl:30][C:19]1[C:9]2[C:10]3[CH:15]=[C:14]([C:16]#[N:17])[N+:13]([O-:18])=[CH:12][C:11]=3[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:25])([CH3:24])[CH3:1])[C:8]=2[N:22]=[CH:21][CH:20]=1.[Cl:30][C:21]1[CH:20]=[CH:19][C:9]2[C:10]3[CH:15]=[C:14]([C:16]#[N:17])[N+:13]([O-:18])=[CH:12][C:11]=3[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:25])([CH3:24])[CH3:1])[C:8]=2[N:22]=1

참가 물질

7

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 866534929-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile-1,7-dioxide

생성물 2

HCID 670274914-Chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile-7-oxideHCID 866534912-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile-7-oxide

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile-1,7-dioxide (2.1 g, 5.9 mmol) in N,N-dimethylformamide (50 mL) was treated with methanesulfonyl chloride (0.78 mL, 10.0 mmol), and the reaction mixture was stirred at ambient temperature for 7 hours. The reaction mixture was then diluted with ethyl acetate (150 mL) and water (200 mL). The layers were separated and the organic layer was dried over sodium sulfate, filtered, concentrated in vacuo, and purified by flash chromatography (silica, 40 g, ISCO, 5-85% ethyl acetate in heptane) to afford the title compound as a 6.5:1 mixture with 2-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile-7-oxide respectively as an off-white solid (1.7 g, 77%). The mixture was triturated in ethyl acetate (10 mL) overnight and the remaining solid was collected by vacuum filtration and washed with ethyl acetate (5 mL) to afford the title compound with >98% purity. 1H NMR (400 MHz, CDCl3) δ 8.86 (s, 1H), 8.39 (d, J=6.4, 1H), 8.27 (s, 1H), 7.94 (d, J=8.1, 1H), 7.32 (dd, J=7.9, 6.5, 1H), 6.55 (s, 2H), 3.73 (t, J=8.0, 2H), 0.93 (t, J=8.0, 2H), −0.04 (s, 9H).

후처리

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography (silica, 40 g, ISCO, 5-85% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-d1bc207c6bcc4625851d5e89e175cfab
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440976B2

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