Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | HCID 11576170 | HCID 11576170 | — |
| Reactant | (Dimethyl sulfide)trihydroboron | HCID 12423031 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 11575891 | HCID 11575891 | 73.5% |
Reaction Steps
A solution of 7 mg (0.0153 mmol) of N,N-dimethyl-3-[2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-indol-1-ylmethyl]-benzamide (example 34) in 0.2 mL of THF was treated with 0.006 mL (0.031 mmol) of borane dimethylsulfide. The mixture was stirred at 70° C. for 10 hrs, treated with MeOH, and concentrated. Column chromatography on silica gel with n-heptane/EtOAc 4:1 to 1:1 yielded 5 mg (72%) of 2-[1-(3-dimethylaminomethyl-benzyl)-2-methyl-1H-indol-5-yl]-1,1,1,3,3, 3-hexafluoro-propan-2-ol, light yellow oil, MS: 445 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07485652B2 |
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| Source dataset | uspto-grants-2009_02 |
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| ORD ID | ord-d7047b1bcebd4bdfba9f4ae2fd74a894 |
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| Source note | uspto-grants-2009_02 |
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