5-Bromo-2-methylpyridine → (2R)-N,N-dibenzyl-8-(6-methylpyridin-3-yl)-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 1099419Notes

Reaction equation

HRID 1099419 reaction equation
[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@H:9]1[CH2:18][C:17]2[C:16](B(O)O)=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:30]1[CH:31]=[CH:32][C:33]([CH3:36])=[N:34][CH:35]=1>>[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@@H:9]1[CH2:10][CH2:11][C:12]2[C:17](=[C:16]([C:30]3[CH:35]=[N:34][C:33]([CH3:36])=[CH:32][CH:31]=3)[CH:15]=[CH:14][CH:13]=2)[CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 12010205-Bromo-2-methylpyridineHCID 59354908[(7R)-7-(dibenzylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]boronic acid

Product 1

HCID 25116055(2R)-N,N-dibenzyl-8-(6-methylpyridin-3-yl)-1,2,3,4-tetrahydronaphthalen-2-amineYield 63%

Procedure

The title compound was synthesized as described for Intermediate example I-48 in 63% yield starting from [(7R)-7-(dibenzylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]boronic acid and 5-bromo-2-methylpyridine (1.6 equiv): 1H NMR (400 MHz, CDCl3) δ ppm 8.45 (d, 1 H), 7.48 (dd, 1 H), 7.30-7.36 (m, 4 H), 7.23-7.29 (m, 5 H), 7.07-7.23 (m, 4 H), 7.00 (d, 1 H), 3.63 (s, 4 H), 2.90-3.04 (m, 2 H), 2.74-2.86 (m, 1 H), 2.68-2.73 (m, 2 H), 2.67 (s, 3 H), 2.11-2.19 (m, 1 H), 1.67-1.82 (m, 1 H); MS (ESI) m/z 420[M+H+].

Sources & evidence

ORD record
ord-9eb1e9e3637c4119aca9a281b83f80b6
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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