Pyridine → 1-cyclopropyl-3-ethyl-6-{1-[4-(methylsulfonyl)phenyl]-1H-pyrazol-5-yl}-1H-indazole

HRID 2113721Notes

Reaction equation

HRID 2113721 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:16]([C:17]4[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=4)[N:15]=[CH:14][CH:13]=3)=[CH:9][CH:10]=2)[NH:5][N:4]=1)[CH3:2].[CH:27]1(B(O)O)[CH2:29][CH2:28]1.C(N(CC)CC)C.N1C=CC=CC=1>O1CCCC1>[CH:27]1([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[C:8]([C:12]4[N:16]([C:17]5[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=5)[N:15]=[CH:14][CH:13]=4)[CH:7]=3)[C:3]([CH2:1][CH3:2])=[N:4]2)[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 2760897Cyclopropylboronic acidHCID 178437987HCID 178437987, compound

Product 1

HCID 598108151-cyclopropyl-3-ethyl-6-{1-[4-(methylsulfonyl)phenyl]-1H-pyrazol-5-yl}-1H-indazoleYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-ethyl-6-{1-[4-(methylsulfonyl)phenyl]-1H-pyrazol-5-yl}-1H-indazole (20 mg, 0.054 mmol), cyclopropylboronic acid (14 mg, 0.16 mmol), cupric acetate (20 mg, 0.11 mmol), triethylamine (0.038 mL, 0.27 mmol), pyridine (0.035 mL, 0.44 mmol), and tetrahydrofuran (2.0 mL) were added to a 10 mL sealed tube. The mixture was subjected to microwave radiation (300 watts, 140° C.) for 10 minutes. The solvent was removed and the residue was extracted with ethyl acetate (10 mL). The extract was washed with saturated sodium bicarbonate solution (2×50 mL). Concentration afforded 22 mg (40%) of 1-cyclopropyl-3-ethyl-6-{1-[4-(methylsulfonyl)phenyl]-1H-pyrazol-5-yl}-1H-indazole. LC/MS (EI) tR 4.15 (Method A), m/z 407.1 (M++1). 1H NMR (CDCl3) δ 1.1 (m, 4H); 1.4 (t, 3H); 2.9 (m, 2H); 3.1 (s, 3H); 3.5 (m, 1H): 6.5 (s, 1H); 6.9 (d, 1H); 7.4 (s, 1H); 7.5 (d, 1H); 7.6 (d, 2H); 7.8 (s, 1H); 7.9 (d, 2H).

Workup

  1. customsealed tube
  2. customThe solvent was removed
  3. extractionthe residue was extracted with ethyl acetate (10 mL)
  4. washThe extract was washed with saturated sodium bicarbonate solution (2×50 mL)
  5. concentrationConcentration

Sources & evidence

ORD record
ord-bed6abc145684ac0897ea5b9763aa0f7
Source dataset
uspto-grants-2008_10
Patent number
US07432266B2

Reaction notes

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