(S,E)-4'-fluoro-7'-(2-fluoropyridin-3-yl)-2'-(2-(3-methyloxetan-3-yl)vinyl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine → (S)-4'-fluoro-7'-(2-fluoropyridin-3-yl)-2'-(2-(3-methyloxetan-3-yl)ethyl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

HRID 335852Notes

Reaction equation

HRID 335852 reaction equation
[F:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][C:10]([C:16]4[C:17]([F:22])=[N:18][CH:19]=[CH:20][CH:21]=4)=[CH:11][CH:12]=3)[C@@:7]3([CH2:26][O:25][C:24]([NH2:27])=[N:23]3)[C:6]=2[CH:5]=[C:4](/[CH:28]=[CH:29]/[C:30]2([CH3:34])[CH2:33][O:32][CH2:31]2)[CH:3]=1>[Pd].CCO>[F:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][C:10]([C:16]4[C:17]([F:22])=[N:18][CH:19]=[CH:20][CH:21]=4)=[CH:11][CH:12]=3)[C@@:7]3([CH2:26][O:25][C:24]([NH2:27])=[N:23]3)[C:6]=2[CH:5]=[C:4]([CH2:28][CH2:29][C:30]2([CH3:34])[CH2:31][O:32][CH2:33]2)[CH:3]=1

Participants

4

Reactant 1

HCID 67383212(S,E)-4'-fluoro-7'-(2-fluoropyridin-3-yl)-2'-(2-(3-methyloxetan-3-yl)vinyl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Product 1

HCID 58466173(S)-4'-fluoro-7'-(2-fluoropyridin-3-yl)-2'-(2-(3-methyloxetan-3-yl)ethyl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a reaction vessel charged with (S,E)-4′-fluoro-7′-(2-fluoropyridin-3-yl)-2′-(2-(3-methyloxetan-3-yl)vinyl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (38 mg, 0.082 mmol) and Pd/C (5%) (30 mg, 0.082 mmol) was added EtOH (1.5 mL). The reaction mixture was purged with hydrogen gas for 5 minutes and then maintained under 1 atm of hydrogen gas for 4 hours. The mixture was filtered through celite and the derived filtrate concentrated to provide (S)-4′-fluoro-7′-(2-fluoropyridin-3-yl)-2′-(2-(3-methyloxetan-3-yl)ethyl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine as white solid.

Workup

  1. customThe reaction mixture was purged with hydrogen gas for 5 minutes
  2. temperaturemaintained under 1 atm of hydrogen gas for 4 hours
  3. filtrationThe mixture was filtered through celite
  4. concentrationthe derived filtrate concentrated

Sources & evidence

ORD record
ord-4470ff27803a433499610724f03b2a0a
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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