홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Lithium hexamethyldisilazane → 7-bromo-N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79441
노트
인쇄 미리보기

반응식

HRID 79441 반응식
[CH2:1]([C:3]1[C:11]2[C:10]([NH2:12])=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]([CH2:13][C:14]2[CH:18]=[CH:17][N:16]([CH2:19][CH3:20])[N:15]=2)[N:4]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Br:31][C:32]1[CH:37]=[CH:36][N:35]2[C:38]([C:41](OC)=[O:42])=[CH:39][N:40]=[C:34]2[CH:33]=1>C1COCC1.CO.C(Cl)Cl>[Br:31][C:32]1[CH:37]=[CH:36][N:35]2[C:38]([C:41]([NH:12][C:10]3[CH:9]=[CH:8][CH:7]=[C:6]4[C:11]=3[C:3]([CH2:1][CH3:2])=[N:4][N:5]4[CH2:13][C:14]3[CH:18]=[CH:17][N:16]([CH2:19][CH3:20])[N:15]=3)=[O:42])=[CH:39][N:40]=[C:34]2[CH:33]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 2733832Lithium hexamethyldisilazaneHCID 67259752Methyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylateHCID 672598083-Ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine

생성물 1

HCID 672612817-bromo-N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide수율 80.9%

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
2회
HCID 21226129Dichloromethane methanol용매

실험 절차

To a solution 3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine (328 mg, 1.22 mmol) in anhydrous THF (3 mL) was added under a nitrogen atmosphere at ambient temperature lithium bis(trimethylsilyl)amide (1.0 M in THF, 1.15 mL). The resulting mixture was stirred at ambient temperature for 10 minutes, then added dropwise to a chilled (ice-water bath) solution of methyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate (140 mg, 0.55 mmol) in anhydrous THF (3 mL). The cold bath was removed, and the reaction mixture was allowed to warm to ambient temperature, and quenched with water. The resulting suspension was extracted thoroughly with DCM, the combined organic extracts were dried over anhydrous sodium sulfate, and concentrated to afford the crude product. The crude product was subjected to preparative thin-layer chromatography on silica with 5% MeOH-DCM as eluent to afford 219 mg of desired product as a yellow solid.

후처리

  1. additionadded dropwise to
  2. customThe cold bath was removed
  3. temperatureto warm to ambient temperature
  4. customquenched with water
  5. extractionThe resulting suspension was extracted thoroughly with DCM
  6. dry with materialthe combined organic extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto afford the crude product

출처 및 근거

ORD 기록
ord-f75a56197e3d4287b252b3ec5dd6f04d
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08841455B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트