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

HRID 60316

反応式

HRID 60316 の反応式
[Br:1][C:2]1[N+:10]([O-:11])=[CH:9][C:8]2[N:7]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]3=[N+:20]([O-])[CH:21]=[CH:22][CH:23]=[C:5]3[C:4]=2[CH:3]=1.CS([Cl:29])(=O)=O>CN(C)C=O.C(OCC)(=O)C.O>[Br:1][C:2]1[N+:10]([O-:11])=[CH:9][C:8]2[N:7]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]3[N:20]=[CH:21][CH:22]=[C:23]([Cl:29])[C:5]=3[C:4]=2[CH:3]=1.[Br:1][C:2]1[N+:10]([O-:11])=[CH:9][C:8]2[N:7]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]3[N:20]=[C:21]([Cl:29])[CH:22]=[CH:23][C:5]=3[C:4]=2[CH:3]=1

参加物

7

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 866560446-Bromo-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-1,7-dioxide

生成物 2

HCID 866560456-Bromo-4-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-7-oxideHCID 866560466-bromo-2-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-7-oxide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 6-bromo-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-1,7-dioxide (1 g, 2.4 mmol) in N,N-dimethylformamide (19 mL) was treated with methanesulfonyl chloride (0.38 mL, 4.9 mmol) and the reaction mixture was stirred at ambient temperature for 3 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 4:1 mixture with 6-bromo-2-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-7-oxide respectively as an off-white solid (100 mg, 10%). The mixture was used in the next step without any further purification.

後処理

  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)

出典と根拠

ORDレコード
ord-a0a756f94293465f820dd26555d9f59d
出典データセット
uspto-grants-2016_09
特許番号
US09440976B2

関連ノート

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