HCID 90461169, compound → HCID 178450090, compound

HRID 1053640Notes

Reaction equation

HRID 1053640 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11](C1CCCCO1)[N:10]=[C:9]2[CH:21]=[O:22])[CH:2]([CH3:4])[CH3:3]>Cl.C(O)C.O1CCOCC1>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[CH:21]=[O:22])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 1

HCID 90461169HCID 90461169, compound

Product 1

HCID 178450090HCID 178450090, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-iso-butoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carbaldehyde (250 mg, 0.83 mmol, 1.00 equiv) in 12N hydrochloric acid (3 mL), ethanol (3 mL) and 1,4-dioxane (6 mL) was stirred overnight at room temperature. The reaction mixture was concentrated under vacuum and the pH value of the solution was adjusted to 8 with saturated sodium bicarbonate solution. The resulting mixture was extracted with 3×50 mL of dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 60-100% of ethyl acetate in petroleum ether to yield 110 mg (61%) of 5-iso-butoxy-1H-indazole-3-carbaldehyde as a yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 10.16 (s, 1H), 7.61 (d, J=9.0 Hz, 1H), 7.48 (d, J=2.1 Hz, 1H), 7.14 (dd, J=9.0 Hz, 2.1 Hz, 1H), 3.80 (d, J=6.6 Hz, 1H), 2.10-2.05 (m, 1H), 1.01 (d, J=6.6 Hz, 6H) ppm. LCMS (method D, ESI): RT=1.50 min, m/z=219.1 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. extractionThe resulting mixture was extracted with 3×50 mL of dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified on a silica gel column
  6. washeluted with 60-100% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-011282f1d0a34a85919ea564274f17e6
Source dataset
uspto-grants-2016_07
Patent number
US09394258B2

Reaction notes

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