4-Benzyloxy-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide → 4-hydroxy-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

HRID 1177202Notes

Reaction equation

HRID 1177202 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([C:10]2[CH:21]=[C:20]([O:22]CC3C=CC=CC=3)[C:13]3[CH2:14][CH:15]([CH2:17][O:18][CH3:19])[O:16][C:12]=3[CH:11]=2)=[O:9])=[N:3]1>CCOC(C)=O.[Pd]>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([C:10]2[CH:21]=[C:20]([OH:22])[C:13]3[CH2:14][CH:15]([CH2:17][O:18][CH3:19])[O:16][C:12]=3[CH:11]=2)=[O:9])=[N:3]1

Participants

4

Reactant 1

HCID 595600244-Benzyloxy-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

Product 1

HCID 595601864-hydroxy-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amideYield 102.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% Pd on Carbon (100 mg) was added to a solution of 4-benzyloxy-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide (204c) (640 mg, 1.63 mmol) in EtOAc (15 mL). The reaction mixture was stirred under H2 balloon overnight. The mixture was filtered through Celite, washed with EtOAc and concentrated to give a white solid (508 mg, 100% yield). 1H NMR (400 MHz, CDCl3) δ 8.77 (s, 1 H) 7.96 (s, 1 H) 7.28 (d, J=2.27 Hz, 1 H) 6.98 (s, 1 H) 6.82 (s, 1 H) 6.78 (d, J=2.27 Hz, 1 H) 4.98-5.07 (m, 1 H) 3.76 (s, 3 H) 3.56-3.65 (m, 2 H) 3.44 (s, 3 H) 3.25 (dd, J=15.92, 9.60 Hz, 1 H) 2.97 (dd, J=16.04, 7.20 Hz, 1 H); LCMS for C15H17N3O4 m/z 304.00 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with EtOAc
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9ee8ae507b524d5298708746eab1778a
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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