(6-Fluoro-5-methylpyridin-3-yl)boronic acid → HCID 25114913, compound

HRID 1099404Notes

Reaction equation

HRID 1099404 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5](B(O)O)=[CH:4][C:3]=1[CH3:11].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:5]2[CH:6]=[N:7][C:2]([F:1])=[C:3]([CH3:11])[CH:4]=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 17750247(6-Fluoro-5-methylpyridin-3-yl)boronic acidHCID 25053925(3S)-3-(Dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate

Product 1

HCID 25114913HCID 25114913, compoundYield 79%

Procedure

The title compound was synthesized as described for Intermediate example I-2 in 79% yield, starting from 6-fluoro-5-methylpyridin-3-ylboronic acid (1.7 equiv) and (3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate: 1H NMR (400 MHz, CDCl3) δ ppm 7.98 (s, 1 H), 7.50 (dd, 1 H), 7.28-7.36 (m, 8 H), 7.17-7.26 (m, 2 H), 7.14 (t, 1 H), 6.84 (d, 1 H), 6.74 (d, 1 H), 4.32-4.42 (m, 1 H), 4.03 (t, 1 H), 3.65-3.76 (m, 4 H), 3.11-3.25 (m, 1 H), 2.73-2.85 (m, 1 H), 2.61 (dd, 1 H), 2.36 (s, 3 H); MS (ESI) m/z 439[M+H+].

Sources & evidence

ORD record
ord-61a4f4d39fa945e687f3f3e179d9ea67
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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