Potassium Carbonate → Tert-butyl 5-bromo-3-(2-(dimethylamino)acetamido)-1h-indazole-1-carboxylate

HRID 1752569노트

반응식

HRID 1752569 반응식
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Br:11])[CH:9]=2)[N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:26][N:27]([CH3:32])[CH2:28][C:29](Cl)=[O:30]>O1CCCC1>[Br:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:3]=[C:2]2[NH:1][C:29](=[O:30])[CH2:28][N:27]([CH3:32])[CH3:26]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 139949912-(Dimethylamino)acetyl chloride hydrochlorideHCID 58287777tert-butyl 3-amino-5-bromo-1H-indazole-1-carboxylate

생성물 1

HCID 68735653Tert-butyl 5-bromo-3-(2-(dimethylamino)acetamido)-1h-indazole-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of Example 282B (24.43 g, 78 mmol), potassium carbonate (81 g, 587 mmol) and 2-(dimethylamino)acetyl chloride hydrochloride (43.3 g, 274 mmol) was added tetrahydrofuran (200 mL). The reaction mixture was stirred at room temperature for about 2 hours. The reaction mixture was filtered and the filtrate was washed with water (50 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×100 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with methanol in dichloromethane (5%) to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.72 (s, 1H), 8.19 (d, 1H, J=1.6), 8.03 (d, 1H, J=9.0), 7.76 (dd, 1H, J=2.0, 9.0), 3.22 (s, 2H), 2.32 (s, 6H), 1.63 (s, 9H).

후처리

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate was washed with water (50 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane (3×100 mL)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with methanol in dichloromethane (5%)

출처 및 근거

ORD 기록
ord-1c6964eb952d4e39b514d7bb7a278d2d
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163007B2

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