(6-Methoxypyridin-3-yl)boronic acid → (3S)-N,N-dibenzyl-5-(6-methoxypyridin-3-yl)chroman-3-amine

HRID 1099400Notes

Reaction equation

HRID 1099400 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[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:6]2[CH:5]=[N:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=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 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 25053925(3S)-3-(Dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate

Product 1

HCID 25114481(3S)-N,N-dibenzyl-5-(6-methoxypyridin-3-yl)chroman-3-amineYield 84%

Procedure

The title compound was synthesized as described for Intermediate example I-2 in 84% yield, starting from 2-methoxy-5-pyridineboronic acid (1.7 equiv) and (3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate; MS (ESI) m/z 437[M+H+].

Sources & evidence

ORD record
ord-f5f196c9e56b4f419681ab0c1fcb81ca
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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