Potassium Carbonate → HCID 59810800, compound

HRID 2113726Notes

Reaction equation

HRID 2113726 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][O:10][CH3:11].[CH:12]1([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:24]4[N:28]([C:29]5[CH:30]=[C:31]([OH:35])[CH:32]=[CH:33][CH:34]=5)[N:27]=[CH:26][CH:25]=4)[CH:22]=3)[C:17]([CH2:36][CH3:37])=[N:16]2)[CH2:14][CH2:13]1.O.C(#N)C>CN(C)C=O>[CH:12]1([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:24]4[N:28]([C:29]5[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH2:8][CH2:9][O:10][CH3:11])[CH:30]=5)[N:27]=[CH:26][CH:25]=4)[CH:22]=3)[C:17]([CH2:36][CH3:37])=[N:16]2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 18373917Acetonitrile--water (1/1)HCID 59810784HCID 59810784, compound

Product 1

HCID 59810800HCID 59810800, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (60.2 mg, 4.36 mmol), and 1-bromo-2-methoxyethane (40.9 μl, 4.36 mmol) were added to a solution of 3-[5-(1-cyclopropyl-3-ethyl-1H-indazol-6-yl)-1H-pyrazol-1-yl]phenol (50 mg, 1.0 mmol) in N, N-dimethylformamide (3 mL), and the resulting mixture was stirred at 60° C. for 16 hours, then at 80° C. for a further 24 hours. After cooling, the reaction mixture was diluted by the addition of water/acetonitrile (1.0 mL), which was then filtered. The filtrate was purified by preparative HPLC (C18 column, 30×100 mm) using a gradient of 35-80% acetonitrile:water (with 0.1% formic acid) as the eluent at a flow rate of 45 mL/min to afford 24 mg (40%) of 1-cyclopropyl-3-ethyl-6-{1-[3-(2-methoxyethoxy)phenyl]-1H-pyrazol-5-yl}-1H-indazole. LC/MS (EI) tR 4.3 (Method E), m/z 403.2 (M++1). 1H NMR (CDCl3) δ 1.0 (m, 4H); 1.4 (t, 3H); 3.0 (q, 2H) 3.5 (m, 4H); 3.7 (d, 2H); 4.1 (d, 2H) 6.6 (s, 1H); 6.8-6.9 (dd, 2H); 7.1 (m, 2H); 7.2 (m, 1H); 7.3 (s, 1H); 7.5 (d, 1H); 7.8 (s, 1H).

Workup

  1. waitat 80° C. for a further 24 hours
  2. temperatureAfter cooling
  3. filtrationwas then filtered
  4. customThe filtrate was purified by preparative HPLC (C18 column, 30×100 mm)

Sources & evidence

ORD record
ord-e0d785874c5e4f81ab8c29e9a54c28ce
Source dataset
uspto-grants-2008_10
Patent number
US07432266B2

Reaction notes

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