Triphenylphosphine → HCID 58763426, compound
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.O[CH2:35][CH2:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][C:38]=1[C:46]([O:48][CH3:49])=[O:47].[C:50]([OH:53])(=[S:52])[CH3:51]>C1COCC1>[C:50]([S:52][CH2:35][CH2:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][C:38]=1[C:46]([O:48][CH3:49])=[O:47])(=[O:53])[CH3:51]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of triphenylphosphine (1.196 g, 4.56 mmol) in THF (10 mL) was added diisopropyl azodicarboxylate (0.9 mL; 4.56 mmol) at 0° C., and the mixture was stirred at 0° C. for 30 minutes. A solution of methyl 3-(2-hydroxyethyl)-1H-indole-2-carboxylate (1.000 g of the above material) and thioacetic acid (0.34 mL, 4.76 mmol) in THF (5 mL) was dropwise added to the mixture at 0° C. The reaction mixture was stirred at 0° C. for 2 hours. The solvent was removed under a reduced pressure and the residue was purified by column chromatography (5 to 10% EtOAc in hexanes) to afford methyl 3-[2-(acetylthio)ethyl]-1H-indole-2-carboxylate (0.864 g, 63% for the three steps) as a white solid: 1H NMR (DMSO-d6) 2.35 (s, 3H), 3.10–3.16 (m, 2H), 3.28–3.35 (m, 2H), 3.92 (s, 3H), 7.13 (t, J=7.3 Hz, 1H), 7.31 (t, J=7.5 Hz, 1H), 7.47 (d, J=8.3 Hz, 1H), 7.77 (d, J=8.1 Hz, 1H).
Workup
- stirringThe reaction mixture was stirred at 0° C. for 2 hours
- customThe solvent was removed under a reduced pressure
- customthe residue was purified by column chromatography (5 to 10% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-d20186da0de4448088144b5f22d50dd0
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07148250B2
Reaction notes
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