HCID 86680428, compound → HCID 86680429, compound

HRID 1023189Notes

Reaction equation

HRID 1023189 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](/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:14]=2)[CH:9]=[N:8]1>CO.[Pd]>[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]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:14]=2)[CH:9]=[N:8]1

Participants

4

Reactant 1

HCID 86680428HCID 86680428, compound

Product 1

HCID 86680429HCID 86680429, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A stirred solution of (E)-ethyl 3-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)acrylate (0.78 g, 2.60 mmol) in MeOH (30 mL) and Pd/C (100 mg, 0.094 mmol) was stirred under hydrogen atmosphere overnight. The reaction mixture was filtered through celite, and the filtrate was concentrated and dried to give ethyl 3-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)propanoate (0.59 g, 75%), used without further purification. 1HNMR: 400 MHz, DMSO-d6: δ 1.13-1.15 (m, 3H), 1.56-1.57 (m, 2H), 1.58-1.59 (m, 1H), 1.93-2.05 (m, 2H), 2.39-2.50 (m, 1H), 2.63-2.69 (m, 2H), 2.94-2.96 (m, 2H), 3.58 (s, 1H), 3.71-3.76 (m, 1H), 3.86-3.89 (m, 1H), 4.04 (q, J=6.80 Hz, 2H), 5.79-5.80 (m, 1H), 7.29-7.31 (m, 1H), 7.57-7.62 (m, 2H), 8.18 (s, 1H). LCMS: RT 0.99 min; LCMS (ES-API), m/z 219 (M-THP).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customdried

Sources & evidence

ORD record
ord-1d94c0f9293149b19a51012d4513ae7a
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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