Sodium hydride → HCID 71625636, 화합물

HRID 589601

반응식

HRID 589601 반응식
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19](Cl)(=[O:21])=[O:20]>C1COCC1>[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[S:19]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=2)(=[O:21])=[O:20])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 1379281H-Indole, 6-methyl-HCID 3787675Pyridine-2-sulfonyl Chloride

생성물 1

HCID 71625636HCID 71625636, 화합물수율 57.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

6-Methylindole (42) (7.34 g, 56.0 mmol) was added in portions to a mixture of sodium hydride (3.36 g, 84.0 mmol) in THF (80 mL) at 0° C. After 15 min, pyridine-2-sulfonyl chloride (43) (10.0 g, 56.0 mmol) was added, and the reaction was allowed to warm to rt and stirred overnight under N2. The reaction mixture was then quenched with ice water and extracted with EtOAc. The organic layers were combined, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with a linear gradient ranging from 0 to 40% EtOAc-hexanes to provide 8.8 g (57%) of product 44 as a brown gum. 1H NMR (300 MHz, CDCl3) δ 2.44 (s, 3H), 6.62 (dd, J=1, 4 Hz, 1H), 7.03-7.06 (m, 1H), 7.41 (d, J=8 Hz, 1H), 7.41-7.45 (m, 1H), 7.59 (d, J=4 Hz, 1H), 7.79-7.81 (m, 1H), 7.84-7.90 (m, 1H), 8.10 (dt, J=1, 8 Hz, 1H), 8.58-8.60 (m, 1H). LC-MS (CI): m/z 273.0 [(M+H)+ C14H12N2O2S requires 272.06].

후처리

  1. customThe reaction mixture was then quenched with ice water
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography
  6. washeluting with a linear gradient

출처 및 근거

ORD 기록
ord-bf1088f376d1480fbf73035e44118c5d
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233921B2

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