6-Fluoroindole → (2S,3S)-3-(6-fluoro-1H-indol-1-yl)-3-(3-fluorophenyl)propane-1,2-diol

HRID 2110380Notes

Reaction equation

HRID 2110380 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[F:11][C:12]1[CH:13]=[C:14]([C@H:18]2[O:20][C@@H:19]2[CH2:21][OH:22])[CH:15]=[CH:16][CH:17]=1>>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[C@@H:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([F:11])[CH:13]=2)[C@H:19]([OH:20])[CH2:21][OH:22])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 3512786-FluoroindoleHCID 45142226[(2R,3R)-3-(3-fluorophenyl)oxiran-2-yl]methanol

Product 1

HCID 68903046(2S,3S)-3-(6-fluoro-1H-indol-1-yl)-3-(3-fluorophenyl)propane-1,2-diol

Procedure

In an analogous manner to EXAMPLE 117, step 5. (2S,3S)-3-(6-fluoro-1H-indol-1-yl)-3-(3-fluorophenyl)propane-1,2-diol was prepared from 6-fluoro-1H-indole and [(2R,3R)-3-(3-fluorophenyl)oxiran-2-yl]methanol (EXAMPLE 47 step 3). MS (ESI) m/z 304.

Sources & evidence

ORD record
ord-2ba8a0cd37844438b4934995a7ccbfe7
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

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