(2-Methoxypyridin-3-yl)boronic acid → HCID 25114690, compound

HRID 1099402Notes

Reaction equation

HRID 1099402 reaction equation
[CH3:1][O:2][C:3]1[C:8](B(O)O)=[CH:7][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:8]2[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][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 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 25053925(3S)-3-(Dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate

Product 1

HCID 25114690HCID 25114690, compoundYield 93%

Procedure

The title compound was synthesized as described for Intermediate example I-2 in 93% yield, starting from 2-methoxypyridine-3-boronic acid and (3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate. The reaction mixture was irradiated in a microwave at 150° C. for 1 h; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.52 (dd, 1 H), 7.25-7.34 (m, 9 H), 7.16-7.24 (m, 2 H), 7.04-7.14 (m, 2 H), 6.76 (d, 1 H), 6.68 (d, 1 H), 4.25-4.35 (m, 1 H), 4.05 (t, 1 H), 3.80 (s, 3 H), 3.55-3.70 (m, 4 H), 2.93-3.04 (m, 1 H), 2.55-2.84 (m, 1 H), 2.27-2.38 (m, 1 H); MS (ESI) m/z 437[M+H+].

Workup

  1. customThe reaction mixture was irradiated in a microwave at 150° C. for 1 h

Sources & evidence

ORD record
ord-584cd8b178ed42e3928c6320028749d4
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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