Sodium Iodide → 3-(cyclohex-1-en-1-yl)-1-cyclopentyl-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one

HRID 2206062Notes

Reaction equation

HRID 2206062 reaction equation
Cl[Si](C)(C)C.[I-].[Na+].[C:8]1([C:14]2[C:18]3[C:19]([O:23]C)=[N:20][CH:21]=[CH:22][C:17]=3[N:16]([CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[N:15]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1.C(OCC)(=O)C>C(#N)C.O.C1COCC1>[C:8]1([C:14]2[C:18]3[C:19](=[O:23])[NH:20][CH:21]=[CH:22][C:17]=3[N:16]([CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29]3)[N:15]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 8857Ethyl AcetateHCID 1179877963-(cyclohex-1-en-1-yl)-1-cyclopentyl-4-methoxy-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 1370105863-(cyclohex-1-en-1-yl)-1-cyclopentyl-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution (1.0 mL) of 1-cyclopentyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl trifluoromethanesulfonate (29.2 mg) obtained in Step C of Example 12, 2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (16.7 mg) and tetrakistriphenylphosphine palladium (18.5 mg) in DME was added 2N sodium carbonate (120 μl), and the mixture was reacted at 100° C. for 6 hr. To the reaction mixture were added ethyl acetate (4 mL), THF (1 mL) and water (1 mL), the mixture was stirred for 5 min, and the organic layer was separated, and concentrated by air-blowing. The residue was purified by preparative high-performance liquid chromatography (C18, mobile phase: acetonitrile/10 mM aqueous ammonium bicarbonate solution) to give 3-(cyclohex-1-en-1-yl)-1-cyclopentyl-4-methoxy-1H-pyrazolo[4,3-c]pyridine. A solution (1.0 mL) of chloro(trimethyl)silane (10.2 μl) and sodium iodide (12.0 mg) in acetonitrile was added to 3-(cyclohex-1-en-1-yl)-1-cyclopentyl-4-methoxy-1H-pyrazolo[4,3-c]pyridine, and the mixture was reacted at 60° C. for 1 hr. To the reaction mixture were added ethyl acetate (4 mL), THF (1 mL) and water (1 mL), the mixture was stirred for 5 min, and the organic layer was separated, and concentrated by air-blowing. The residue was purified by preparative high-performance liquid chromatography (C18, mobile phase: acetonitrile/10 mM aqueous ammonium bicarbonate solution) to give the title compound (13.0 mg).

Workup

  1. customthe mixture was reacted at 60° C. for 1 hr
  2. customthe organic layer was separated
  3. concentrationconcentrated by air-blowing
  4. customThe residue was purified by preparative high-performance liquid chromatography (C18, mobile phase: acetonitrile/10 mM aqueous ammonium bicarbonate solution)

Sources & evidence

ORD record
ord-6c523dcaae3445d0b2ae084dcf980a53
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

Loading…