[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonate → 2-[3-(6-Fluoro-1h-indol-3-ylmethyl)-piperidin-1-ylmethyl]-8-methyl-2,3-dihydro-[1,4]dioxino[2,3-f]quinoline
Reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[O:15][CH2:14][C@H:13]([CH2:16]OS(C4C=CC(Br)=CC=4)(=O)=O)[O:12][C:8]3=2)[N:3]=1.[F:28][C:29]1[CH:37]=[C:36]2[C:32]([C:33]([CH2:38][CH:39]3[CH2:44][CH2:43][CH2:42][NH:41][CH2:40]3)=[CH:34][NH:35]2)=[CH:31][CH:30]=1>>[F:28][C:29]1[CH:37]=[C:36]2[C:32]([C:33]([CH2:38][CH:39]3[CH2:44][CH2:43][CH2:42][N:41]([CH2:16][CH:13]4[O:12][C:8]5=[C:9]6[C:4](=[CH:5][CH:6]=[C:7]5[O:15][CH2:14]4)[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]6)[CH2:40]3)=[CH:34][NH:35]2)=[CH:31][CH:30]=1Participants
3
Procedure
This compound was prepared as described for Example 2, using (2R)-4-bromobenzenesulfonic acid 8-methyl-2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-2-ylmethyl ester (0.22 g, 4.9 mmol), 6-fluoro-3-piperidin-3-ylmethyl-1H-indole (0.13 g, 5.9 mmol), to afford 0.11 g (50%) of the (S)-enantiomer of the title compound as a light brown oil. The hydrogen chloride salt was prepared in ethyl acetate and collected as 0.12 g of a yellow solid, m.p. 50° C. (dec).
Workup
- customThis compound was prepared
Sources & evidence
- ORD record
- ord-dc187a46cc9d4b759326bf4e897faf22
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07419986B2
Reaction notes
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