4-[2-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-oxazol-5-yl]-2-isobutyl-6-methyl-pyridine → 2-Ethyl-4-[5-(2-isobutyl-6-methyl-pyridin-4-yl)-oxazol-2-yl]-6-methyl-phenol

HRID 2040833Notes

Reaction equation

HRID 2040833 reaction equation
C([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[O:17][C:18]([C:21]3[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([CH2:28][CH:29]([CH3:31])[CH3:30])[CH:22]=3)=[CH:19][N:20]=2)=[CH:11][C:10]=1[CH2:32][CH3:33])C1C=CC=CC=1>C1COCC1.CCO.[Pd]>[CH2:32]([C:10]1[CH:11]=[C:12]([C:16]2[O:17][C:18]([C:21]3[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([CH2:28][CH:29]([CH3:30])[CH3:31])[CH:22]=3)=[CH:19][N:20]=2)[CH:13]=[C:14]([CH3:15])[C:9]=1[OH:8])[CH3:33]

Participants

5

Reactant 1

HCID 685539084-[2-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-oxazol-5-yl]-2-isobutyl-6-methyl-pyridine

Product 1

HCID 1359642142-Ethyl-4-[5-(2-isobutyl-6-methyl-pyridin-4-yl)-oxazol-2-yl]-6-methyl-phenolYield 47.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[2-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-oxazol-5-yl]-2-isobutyl-6-methyl-pyridine (29 mg, 66 μmol) in THF (0.5 mL) and EtOH (0.5 mL), Pd/C (10 mg, 10% Pd) is added. The mixture is stirred at rt under 1 bar of H2 for 16 h. The catalyst is filtered off and the filtrate is concentrated. The residue is again treated with Pd/C and H2 at rt for 24 h as described before. The catalyst is filtered off and the filtrate is evaporated. The crude product is purified on prep. TLC using heptane:EA 1:1 to give 2-ethyl-4-[5-(2-isobutyl-6-methyl-pyridin-4-yl)-oxazol-2-yl]-6-methyl-phenol (11 mg) as a pale yellow glass; LC-MS: tR=0.97*, [M+1]+=351.11; 1H NMR (CDCl3): δ 0.99 (d, J=6.5 Hz, 6 H), 1.33 (t, J=7.5 Hz, 3 H), 2.12-2.22 (m, 1 H), 2.37 (s, 3 H), 2.63 (s, 3 H), 2.66-2.79 (m, 4 H), 5.35 (s br, 1 H), 7.21 (s, 1 H), 7.29 (s, 1H), 7.58 (s, 1 H), 7.80 (s, 2 H).

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. additionThe residue is again treated with Pd/C and H2 at rt for 24 h
  4. filtrationThe catalyst is filtered off
  5. customthe filtrate is evaporated
  6. customThe crude product is purified on prep

Sources & evidence

ORD record
ord-157fee3791d44ae1b409bcffb364c643
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

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