Triethylamine → 7-Methyl-2-(2-trimethylsilanyl-ethanesulfonyl)-2H-indazole-5-carbaldehyde

HRID 501928노트

반응식

HRID 501928 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:11]=[O:12])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.C(N(CC)CC)C.[CH3:20][Si:21]([CH3:29])([CH3:28])[CH2:22][CH2:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH3:1][C:2]1[C:10]2[C:6](=[CH:7][N:8]([S:24]([CH2:23][CH2:22][Si:21]([CH3:29])([CH3:28])[CH3:20])(=[O:26])=[O:25])[N:9]=2)[CH:5]=[C:4]([CH:11]=[O:12])[CH:3]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 98370862-(Trimethylsilyl)ethane-1-sulfonyl chlorideHCID 184521067-Methyl-1H-indazole-5-carbaldehyde

생성물 1

HCID 211022147-Methyl-2-(2-trimethylsilanyl-ethanesulfonyl)-2H-indazole-5-carbaldehyde수율 77.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of 7-methylindazole 5-aldehyde (3.0 g, 18.7 mmol) in methylene chloride (150 mL) was added triethylamine (7.83 mL, 56.2 mL, 3 equiv) followed by dropwise addition of neat 2-trimethylsilanyl-ethanesulfonyl chloride (5.60 g, 28.1 mmol, 1.5 equiv). The mixture gradually became homogeneous and was allowed to stir at room temperature for 16 h. The solution was concentrated to a minimum amount of methylene chloride and then subjected to flash column chromatography on silica gel (1:4 ethyl acetate/hexanes) to give 4.7 g (77%) of the product as a pale yellow solid. 1H-NMR (CDCl3, 300 MHz) δ 9.98 (s, 1H), 8.77 (s, 1H), 8.09 (s, 1H), 7.64 (s, 1H), 3.64-3.58 (m, 2H), 2.65 (s, 3H), 0.88-0.82 (m, 2H), 0.01 (s, 9H).

후처리

  1. concentrationThe solution was concentrated to a minimum amount of methylene chloride

출처 및 근거

ORD 기록
ord-520bf7df02e4409e8d6d30eb49c0c06b
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772244B2

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