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

HRID 240782Notes

Reaction equation

HRID 240782 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-0f2f629a4aab4194b005184d85b30343
Source dataset
uspto-grants-2014_02
Patent number
US08648069B2

Reaction notes

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