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

HRID 1099397Notes

Reaction equation

HRID 1099397 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B(O)O)[CH:5]=[CH:4][N:3]=1.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:6]2[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=2)[O:22][CH2:21]1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

3

Reactant 2

HCID 27833962-Fluoropyridine-4-boronic acidHCID 25053925(3S)-3-(Dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate

Product 1

HCID 25114263(3S)-N,N-dibenzyl-5-(2-fluoropyridin-4-yl)chroman-3-amineYield 68%

Procedure

The title compound was synthesized as described for Intermediate example I-2 in 68% yield, starting from 2-fluoro-4-pyridinylboronic acid and (3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate. The reaction was irradiated in a microwave at 150° C. for 3 h; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.30 (d, 1 H), 7.33-7.37 (m, 1 H), 7.24-7.33 (m, 8 H), 7.15-7.22 (m, 4 H), 6.79-6.87 (m, 2 H), 4.32-4.38 (m, 1 H), 4.04-4.10 (m, 1 H), 3.61-3.74 (m, 4 H), 2.93-3.10 (m, 2 H), 2.42-2.48 (m, 1 H); MS (ESI) m/z 425[M+H+].

Workup

  1. customThe reaction was irradiated in a microwave at 150° C. for 3 h

Sources & evidence

ORD record
ord-0d382430a89543638b5b6299a711540f
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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