HCID 66793182, compound → HCID 86663366, compound

HRID 1057116Notes

Reaction equation

HRID 1057116 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]#[C:17][CH2:18][OH:19])=[CH:13][CH:14]=2)[CH:9]=[N:8]1>O=[Mn]=O.ClCCl>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]#[C:17][CH:18]=[O:19])=[CH:13][CH:14]=2)[CH:9]=[N:8]1

Participants

4

Reactant 1

HCID 66793182HCID 66793182, compound2×

Product 1

HCID 86663366HCID 86663366, compoundYield 56.9%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A 500 mL three-necked round bottom flask was charged with 3-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)prop-2-yn-1-ol (11.4 g, 44.2 mmol; Intermediate 19), dichloromethane (300 mL) and MnO2 (38.4 g, 442 mmol). The resulting mixture was stirred at room temperature for 16 hours. Upon completion, the reaction mixture was filtered. The filtrate was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (1:100-1:20 EtOAc/petroleum ether) affording the title compound (6.4 g). 1H NMR (400 MHz, DMSO-d6): δ 9.45 (s, 1H), 8.27-8.25 (m, 2H), 7.87 (d, 1H), 7.66 (dd, 1H), 5.86 (dd, 1H), 3.91-3.87 (m, 1H), 3.79-3.72 (m, 1H), 2.40-2.36 (m, 1H), 2.05-1.96 (m, 2H), 1.78-1.72 (m, 1H), 1.61-1.56 (m, 2H); LCMS: 255 (M+H)+.

Workup

  1. filtrationUpon completion, the reaction mixture was filtered
  2. dry with materialThe filtrate was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (1:100-1:20 EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-8c3906f17a5443b7810d690c31bf70bd
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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