N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamide → HCID 178486133、化合物

HRID 1710383

反応式

HRID 1710383 の反応式
[C:1]1([C:7]2[CH:8]=[C:9]3[N:15]=[C:14]([CH2:16][CH2:17][CH:18]4[NH:24][C:23](=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19]4)[NH:13][C:10]3=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrC1C=C2N=C(CCC3NC(=O)CCCC3)NC2=NC=1.[CH3:46][N:47]([CH3:66])[S:48](C1C=CC(B2OC(C)(C)C(C)(C)O2)=CC=1)(=[O:50])=[O:49]>C(=O)([O-])[O-].[Na+].[Na+]>[CH3:46][N:47]([CH3:66])[S:48]([C:4]1[CH:3]=[CH:2][C:1]([C:7]2[CH:8]=[C:9]3[N:15]=[C:14]([CH2:16][CH2:17][CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22][C:23](=[O:25])[NH:24]4)[NH:13][C:10]3=[N:11][CH:12]=2)=[CH:6][CH:5]=1)(=[O:50])=[O:49]

参加物

5

反応物 3

HCID 3868489N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamide2 回HCID 178516005HCID 178516005、化合物2 回HCID 178516006HCID 178516006、化合物2 回

生成物 1

HCID 178486133HCID 178486133、化合物

試薬・触媒・溶媒 1

HCID 10340Sodium Carbonate溶媒

実験手順

The title compound is analogously synthesized as described for 7-[2-(6-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-one (compound B1) from 100 mg of 7-[2-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-one (compound C1), 890 μl of aqueous sodium carbonate solution (strength 2.0 M), 138 mg N,N-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamide (compound C2), and 26 mg of trans-dichloro-bis(tricyclohexyl-phosphine)-palladium(II) at 160° C. for 30 min (microwave irradiation, power ≦300 W). Purification by chromatography on flash silica gel (eluent gradient: dichloromethane/0-10 vol. % ethanol) yields 93 mg of the title compound as a waxy solid. ESI-MS: 442.4 (MH+). TLC: Rf=0.41 (dichloromethane/ethanol 10:1 parts by volume).

後処理

  1. custom(microwave irradiation, power ≦300 W)
  2. customPurification by chromatography on flash silica gel (eluent gradient: dichloromethane/0-10 vol. % ethanol)

出典と根拠

ORDレコード
ord-2954c351b5b34ed2827228a25b0cc440
出典データセット
uspto-grants-2010_09
特許番号
US07790710B2

関連ノート

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