Diphenyl sulfide → HCID 24898113, compound

HRID 1675252Notes

Reaction equation

HRID 1675252 reaction equation
S(C1C=CC=CC=1)C1C=CC=CC=1.[C:14]1([C:19]2[CH:20]=[C:21]([CH:40]=[CH:41][C:42]=2[O:43][C:44]([F:47])([F:46])[F:45])[CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C@@H:30]([C:35]3[CH:39]=[CH:38][O:37][N:36]=3)[CH2:31][C:32]([OH:34])=[O:33])=[CH:26][CH:25]=2)[CH2:18][CH2:17][CH2:16][CH:15]=1>CO.[Pd]>[CH:14]1([C:19]2[CH:20]=[C:21]([CH:40]=[CH:41][C:42]=2[O:43][C:44]([F:46])([F:47])[F:45])[CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C@@H:30]([C:35]3[CH:39]=[CH:38][O:37][N:36]=3)[CH2:31][C:32]([OH:34])=[O:33])=[CH:26][CH:25]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 8766Diphenyl sulfideHCID 59300603HCID 59300603, compound

Product 1

HCID 24898113HCID 24898113, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a suspension of Pd/C (20.0 mg, 10%) with Ph2S (1.0%) in MeOH (5.0 mL), was added 20 (25.0 mg, 0.164 mmol) in MeOH (1.0 mL). The reaction mixture was purged with hydrogen three times. The mixture was then stirred under hydrogen at room temperature overnight. The catalyst was filtered off, and the solvent was evaporated to give the title compound 23. 1H NMR (CD3CN) δ 1.55-2.02 (m, 8H), 2.93 (dd, J=7.3, 16.4 Hz, 1 H), 3.16 (dd, J=7.3, 16.4 Hz, 1 H), 3.33 (m, 1 H), 4.53 (m, 1 H), 5.05 (s, 2 H), 6.24 (d, J=1.7 Hz, 1H), 6.94 (d, J=6.6 Hz, 2H), 7.22-7.26 (m, 4H), 7.49 (d, J=5.0 Hz, 1H), 8.45 (d, J=1.7 Hz, 1H). MS ESI (pos.) m/e: 476 (M+H).

Workup

  1. customThe reaction mixture was purged with hydrogen three times
  2. filtrationThe catalyst was filtered off
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4f1fd26b99fd4dc59ec21bc51d7685fa
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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