(2-Methoxypyridin-4-yl)boronic acid → (3S)-N,N-dibenzyl-5-(2-methoxypyridin-4-yl)chroman-3-amine

HRID 1099398Notes

Reaction equation

HRID 1099398 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](B(O)O)[CH:6]=[CH:5][N:4]=1.FC(F)(F)S(O[C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH2:20][C@H:21]([N:28]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:22][O:23]2)(=O)=O>>[CH2:36]([N:28]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C@H:21]1[CH2:20][C:19]2[C:24](=[CH:25][CH:26]=[CH:27][C:18]=2[C:7]2[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=2)[O:23][CH2:22]1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

3

Reactant 2

HCID 23546919(2-Methoxypyridin-4-yl)boronic acidHCID 25053925(3S)-3-(Dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate

Product 1

HCID 25114477(3S)-N,N-dibenzyl-5-(2-methoxypyridin-4-yl)chroman-3-amineYield 100%

Procedure

The title compound was synthesized as described for Intermediate example I-2 in 100% yield, starting from 2-methoxypyridine-4-boronic acid and (3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.22 (d, 1 H), 7.23-7.34 (m, 8 H), 7.09-7.23 (m, 3 H), 6.96 (dd, 1 H), 6.80 (dd, 1 H), 6.70-6.78 (m, 2 H), 4.31-4.37 (m, 1 H), 4.03-4.10 (m, 1 H), 3.91 (s, 3 H), 3.62-3.73 (m, 4 H), 2.90-3.07 (m, 2 H), 2.43-2.49 (m, 1 H); MS (ESI) m/z 437[M+H+].

Sources & evidence

ORD record
ord-c64beac2b1bd4a31ba9e1d01295bd0cc
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

Loading…