Methanol → HCID 11575891, compound

HRID 346827Notes

Reaction equation

[CH3:1][N:2]([CH3:32])[C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([OH:29])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:17][CH:18]=3)[CH:13]=[C:12]2[CH3:30])[CH:5]=1.CSC.B.CO>C1COCC1>[CH3:1][N:2]([CH2:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([OH:29])([C:25]([F:27])([F:28])[F:26])[C:21]([F:23])([F:22])[F:24])=[CH:17][CH:18]=2)[CH:13]=[C:12]1[CH3:30])[CH3:32]

Participants

Conditions

Temperature: 70 °C

Procedure

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+).

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-bd24e4f61a3d44ceada3878df3c32b3c
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173048B2

Reaction notes

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