3-(benzyloxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzamide → 3-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)-5-[((1S)-1-methyl-2-{[tris(1-methylethyl)silyl]oxy}ethyl)oxy]benzamide

HRID 1175840Notes

Reaction equation

HRID 1175840 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:21]=[C:22]([O:24][C@@H:25]([CH3:38])[CH2:26][O:27][Si:28]([CH:35]([CH3:37])[CH3:36])([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])[CH3:30])[CH:23]=1)[C:12]([NH:14][C:15]1[CH:19]=[CH:18][N:17]([CH3:20])[N:16]=1)=[O:13])C1C=CC=CC=1>[Pd].C1COCC1>[OH:8][C:9]1[CH:10]=[C:11]([CH:21]=[C:22]([O:24][C@@H:25]([CH3:38])[CH2:26][O:27][Si:28]([CH:35]([CH3:37])[CH3:36])([CH:29]([CH3:31])[CH3:30])[CH:32]([CH3:33])[CH3:34])[CH:23]=1)[C:12]([NH:14][C:15]1[CH:19]=[CH:18][N:17]([CH3:20])[N:16]=1)=[O:13]

Participants

4

Reactant 1

HCID 536296203-(benzyloxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzamide

Product 1

HCID 536296193-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)-5-[((1S)-1-methyl-2-{[tris(1-methylethyl)silyl]oxy}ethyl)oxy]benzamideYield 100.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10% Palladium on carbon was added to 3-(benzyloxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzamide (21.7 g, 40.4 mmol) in dry THF (480 mL) under argon. The reaction mixture was degassed and placed under a hydrogen balloon and stirred for 16 hours. The atmosphere was replaced with argon and mixture was filtered through diatomaceous earth then the filtrate evaporated and dried under high vacuum for 1 hour to give the title compound (18.2 g). 1H NMR δ (CDCl3): 1.05 (s, 18H), 1.05-1.1 (m, 3H), 1.3 (d, 3H), 3.7 (m, 1H), 3.8 (s, 3H), 3.9 (m, 1H), 4.5 (m, 1H), 6.6 (s, 1H), 6.8 (s, 1H), 7.0 (m, 2H), 7.20 (s, 1H), 7.3 (s, 1H), 8.7 (s, 1H). m/z 448 (M+H)+, 446 (M−H)−

Workup

  1. customThe reaction mixture was degassed
  2. filtrationwas filtered through diatomaceous earth
  3. customthe filtrate evaporated
  4. customdried under high vacuum for 1 hour

Sources & evidence

ORD record
ord-80a372a9de2f4ef09017c6caed35ec88
Source dataset
uspto-grants-2010_11
Patent number
US07842694B2

Reaction notes

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