2-Fluoropyridine-3-boronic acid → (2R)-N,N-dibenzyl-8-(2-fluoropyridin-3-yl)-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 1099418Notes

Reaction equation

HRID 1099418 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[C:12](Br)[CH:13]=[CH:14][CH:15]=2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:27][C:28]1[C:33](B(O)O)=[CH:32][CH:31]=[CH:30][N:29]=1>>[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[C:12]([C:33]3[C:28]([F:27])=[N:29][CH:30]=[CH:31][CH:32]=3)[CH:13]=[CH:14][CH:15]=2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27832702-Fluoropyridine-3-boronic acidHCID 22082960(2R)-N,N-dibenzyl-8-bromo-1,2,3,4-tetrahydronaphthalen-2-amine

Product 1

HCID 25115833(2R)-N,N-dibenzyl-8-(2-fluoropyridin-3-yl)-1,2,3,4-tetrahydronaphthalen-2-amineYield 75%

Procedure

The title compound was synthesized as described for Intermediate example I-4 in 75% yield, starting from (2R)-N,N-dibenzyl-8-bromo-1,2,3,4-tetrahydronaphthalen-2-amine and 2-fluoropyridine-3-boronic acid; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.29-8.34 (m, 1 H), 7.78-7.89 (m, 1 H), 7.41-7.52 (m, 1 H), 7.21-7.30 (m, 8 H), 7.11-7.21 (m, 4 H), 7.01 (dd, 1 H), 3.51-3.61 (m, 4 H), 2.89-3.00 (m, 1 H), 2.83 (br. s., 1 H), 2.59-2.78 (m, 2 H), 2.34-2.46 (m, 1 H), 2.00-2.12 (m, 1 H), 1.64-1.79 (m, 1 H); MS (ESI) m/z 424[M+H+].

Sources & evidence

ORD record
ord-6555e7e209194615a926e28899468ce5
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

Loading…