Toluene → 2-Benzyl-6-methyl-2,3,3a,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[alpha]pentalen-7-one
Reaction equation
[CH2:1]([N:8]1[CH2:15][CH:14]2[CH:10]([C:11](=[O:20])[C:12]3[C:18](Br)=[CH:17][S:16][C:13]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][Zn]C.C1(C)C=CC=CC=1>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([N:8]1[CH2:15][CH:14]2[CH:10]([C:11](=[O:20])[C:12]3[C:18]([CH3:21])=[CH:17][S:16][C:13]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 22 °C
Procedure
A solution of the product from step e) (2.4 g, 6.89 mmol) in dioxane (34.5 ml) was treated with Pd(dppf)2Cl2 (337 mg, 0.41 mmol) and a 2M solution of dimethylzinc in toluene (6.89 ml, 13.78 mmol) at 102° C. for 1 hour. The reaction was cooled to 22° C. and carefully quenched with sat. NH4Cl (20 ml). After the effervescence subsided, the reaction was extracted with EtOAc (3×50 ml). The combined organic layers were dried (MgSO4) and passed through a plug of silica-gel using 50:50 hexanes:EtOAc to give the subtitle compound (1.9 g, 97%). MS calculated for C17H17NOS+H 284, observed 284.
Workup
- customcarefully quenched with sat. NH4Cl (20 ml)
- extractionthe reaction was extracted with EtOAc (3×50 ml)
- dry with materialThe combined organic layers were dried (MgSO4)
Sources & evidence
- ORD record
- ord-7d45e7a320324e35be752a3a51b923d5
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07981919B2
Reaction notes
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