(3S)-3-(Dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate → (3S)-N,N-dibenzyl-5-(3-methylpyridin-4-yl)chroman-3-amine

HRID 1099399Notes

Reaction equation

HRID 1099399 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1B(O)O.FC(F)(F)S(O[C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH2:19][C@H:20]([N:27]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:21][O:22]2)(=O)=O>>[CH2:35]([N:27]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C@H:20]1[CH2:19][C:18]2[C:23](=[CH:24][CH:25]=[CH:26][C:17]=2[C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[CH3:1])[O:22][CH2:21]1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

3

Reactant 2

HCID 25053925(3S)-3-(Dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonateHCID 44754762(3-Methylpyridin-4-yl)boronic acid

Product 1

HCID 25114479(3S)-N,N-dibenzyl-5-(3-methylpyridin-4-yl)chroman-3-amineYield 76%

Procedure

The title compound was synthesized as described for Intermediate example I-2 in 76% yield, starting from 3-methylpyridine-4-boronic acid and (3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.54 (d, 1 H), 8.46 (dd, 1 H), 7.25-7.32 (m, 8 H), 7.05-7.24 (m, 4 H), 6.76-6.83 (m, 1 H), 6.59-6.64 (m, 1 H), 4.26-4.34 (m, 1 H), 4.04-4.13 (m, 1 H), 3.55-3.68 (m, 4 H), 2.93-3.07 (m, 1 H), 2.34-2.43 (m, 1 H), 2.08-2.22 (m, 1 H), 1.92-2.02 (m, 3 H); MS (ESI) m/z 421[M+H+].

Sources & evidence

ORD record
ord-05ac93c1eddd49b1b6be152988ffd07b
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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