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Lithium Hexamethyldisilazide → n-(7-(4-Bromo-2-chlorophenylamino)-8-chloroimidazo[1,2-a]pyridin-6-yl)cyclopropanesulfonamide

HRID 1161808
ノート
印刷プレビュー

反応式

HRID 1161808 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3=[C:13]([Cl:20])[C:14]4[N:15]([CH:17]=[CH:18][N:19]=4)[CH:16]=[C:11]3[NH:10]C2=O)=[C:4]([Cl:22])[CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH:33]1([S:36](N)(=[O:38])=[O:37])[CH2:35][CH2:34]1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:12]2[C:11]([NH:10][S:36]([CH:33]3[CH2:35][CH2:34]3)(=[O:38])=[O:37])=[CH:16][N:15]3[CH:17]=[CH:18][N:19]=[C:14]3[C:13]=2[Cl:20])=[C:4]([Cl:22])[CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 2733832Lithium HexamethyldisilazideHCID 15765418CyclopropanesulfonamideHCID 595194533-(4-Bromo-2-chlorophenyl)-4-chloro-1H-diimidazo[1,2-a:4',5'-d]pyridin-2(3H)-one

生成物 1

HCID 57344032n-(7-(4-Bromo-2-chlorophenylamino)-8-chloroimidazo[1,2-a]pyridin-6-yl)cyclopropanesulfonamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of the crude product (Step J) in 3 ml anhydrous THF was added LHMDS (0.4 ml, 0.4 mmol, 1M/THF) at 0° C. and the mixture was stirred for 5 min. The cyclopropyl sulfonamide (83 mg, 0.59 mol) was added neat and the mixture was warmed to room temperature and stirred for 15 h. The mixture was quenched with brine, diluted with H2O and extracted using a mixture of EtOAc/THF (3:1). The organic phase was washed with brine and dried with Na2SO4. Subsequent column chromatography (100% EtOAc) gave the title product as a brown oil (36 mg, 20% over the 2 last steps). Rf (100% EtOAc)=0.35. 1H-NMR (500 MHz, MeOH-D3): δ=8.80 (s, 1H), 7.89 (s, 1H), 7.86-7.85 (d, 1H), 7.68-7.66 (dd, 1H), 7.60-7.58 (d, 1H), 7.46 (s, 1H), 1.51-1.37 (m, 2H), 1.23-1.15 (m, 2H).

後処理

  1. stirringstirred for 15 h
  2. customThe mixture was quenched with brine
  3. additiondiluted with H2O
  4. extractionextracted
  5. additiona mixture of EtOAc/THF (3:1)
  6. washThe organic phase was washed with brine
  7. dry with materialdried with Na2SO4

出典と根拠

ORDレコード
ord-5cf294abc3a04ab5b66888779d086790
出典データセット
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07820664B2

反応ノート

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