Ammonia → (4s)-4-N-[5-(Indol-5-yl)-pyridin-3-yl]-1-azatricyclo[3.3.1.13,7]decan-4-amine

HRID 878437Notes

Reaction equation

HRID 878437 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][C@@H:9]2[CH:16]3[CH2:17][N:12]4[CH2:13][CH:14]([CH2:18][CH:10]2[CH2:11]4)[CH2:15]3)[CH:5]=[N:6][CH:7]=1.[NH:19]1[C:27]2[C:22](=[CH:23][C:24](B(O)O)=[CH:25][CH:26]=2)[CH:21]=[CH:20]1.N>>[NH:19]1[C:27]2[C:22](=[CH:23][C:24]([C:2]3[CH:3]=[C:4]([NH:8][C@@H:9]4[CH:16]5[CH2:17][N:12]6[CH2:13][CH:14]([CH2:18][CH:10]4[CH2:11]6)[CH2:15]5)[CH:5]=[N:6][CH:7]=3)=[CH:25][CH:26]=2)[CH:21]=[CH:20]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 27343615-Indolylboronic acidHCID 24987501(4s)-4-N-(5-Bromopyridin-3-yl)-1-azatricyclo[3.3.1.13,7]decan-4-amine

Product 1

HCID 24990478(4s)-4-N-[5-(Indol-5-yl)-pyridin-3-yl]-1-azatricyclo[3.3.1.13,7]decan-4-amine

Procedure

Prepared from the product of Example 69A (150 mg, 0.50 mmol) and 5-indolylboronic acid (160 mg, 1.0 mmol; Aldrich) according to Method E: 1H NMR (300 MHz, methanol-D4) δ ppm 1.59-1.77 (m, 1H), 1.79-1.93 (m, 2H), 1.93-2.07 (m, 2H), 2.28-2.32 (m, 2H), 3.10-3.32 (m, 6H), 3.88 (s, 1H), 6.51 (dd, J=3.0, 0.7 Hz, 1H), 7.27 (d, J=3.4 Hz, 1H), 7.30-7.34 (m, 1H), 7.36 (d, J=1.7 Hz, 1H), 7.47 (d, J=8.3 Hz, 1H), 7.78 (d, J=1.0 Hz, 1H), 7.93 (d, J=2.4 Hz, 1H), 8.03 (d, J=1.7 Hz, 1H). MS (DCI/NH3) m/z=345 (M+H)+.

Sources & evidence

ORD record
ord-9fbb789c41184d64a379d45cb176e6f3
Source dataset
uspto-grants-2015_03
Patent number
US08987453B2

Reaction notes

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