Ammonia → (4r)-4-[5-(1H-Indol-5-yl)pyridin-2-yloxy]-1-azatricyclo[3.3.1.13,7]decane

HRID 1878651Notes

Reaction equation

HRID 1878651 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.Br[C:13]1[CH:14]=[CH:15][C:16]([O:19][C@H:20]2[CH:27]3[CH2:28][N:23]4[CH2:24][CH:25]([CH2:29][CH:21]2[CH2:22]4)[CH2:26]3)=[N:17][CH:18]=1.[NH:30]1[C:38]2[C:33](=[CH:34][C:35](B(O)O)=[CH:36][CH:37]=2)[CH:32]=[CH:31]1.N>>[NH:30]1[C:38]2[C:33](=[CH:34][C:35]([C:13]3[CH:14]=[CH:15][C:16]([O:19][C@H:20]4[CH:27]5[CH2:28][N:23]6[CH2:24][CH:25]([CH2:29][CH:21]4[CH2:22]6)[CH2:26]5)=[N:17][CH:18]=3)=[CH:36][CH:37]=2)[CH:32]=[CH:31]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 27343615-Indolylboronic acidHCID 86621321(4r)-4-(5-Bromopyridin-2-yloxy)-1-azatricyclo[3.3.1.13,7]decane p-toluenesulfonate

Product 1

HCID 86621322(4r)-4-[5-(1H-Indol-5-yl)pyridin-2-yloxy]-1-azatricyclo[3.3.1.13,7]decane

Procedure

Prepared from the product of Example 9F (45 mg, 0.14 mmol) and 5-indolylboronic acid (33 mg, 0.204 mmol; Maybridge) according to Method E: 1H NMR (300 MHz, CHCl3) δ ppm 1.76-1.86 (m, 2H), 2.26 (s, 2H), 2.39 (d, J=11.5 Hz, 2H), 3.26-3.44 (m, 5H), 5.37 (t, J=3.2 Hz, 1H), 6.61 (t, J=2.5 Hz, 1H), 6.85 (d, J=8.5 Hz, 1H), 7.25-7.30 (m, 1H), 7.31-7.41 (m, 1H), 7.48 (d, J=8.5 Hz, 1H), 7.77 (s, 1H), 7.86 (dd, J=8.5, 2.7 Hz, 1H) MS (DCI/NH3) m/z=346 (M+H)+; Anal. Calcd. for C22H22N3O.1.6H2O: C, 70.79; H, 6.80; N, 11.26. Found: C, 70.78; H, 6.44; N, 10.91.

Sources & evidence

ORD record
ord-2e7de7b8eba94572b68f2dbeaed629a9
Source dataset
uspto-grants-2012_11
Patent number
US08314119B2

Reaction notes

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