(6-Methoxypyridin-3-yl)boronic acid → HCID 178488514, compound

HRID 2103698Notes

Reaction equation

HRID 2103698 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([C@H:9]3[CH2:12][C@H:11]([N:13]4[CH2:17]C[CH2:15][C@H:14]4[CH3:18])[CH2:10]3)[S:8][C:4]=2[CH:3]=1.[CH3:21][O:22][C:23]1[N:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.N1C=C(B(O)O)C=NC=1>>[CH:14]([N:13]([C@H:11]1[CH2:10][C@H:9]([C:7]2[S:8][C:4]3[CH:3]=[C:2]([C:26]4[CH:27]=[N:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=4)[CH:20]=[CH:19][C:5]=3[N:6]=2)[CH2:12]1)[CH3:17])([CH3:18])[CH3:15]

Participants

4

Reactant 3

HCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 178461421HCID 178461421, compound

Product 1

HCID 178488514HCID 178488514, compound

Procedure

The title compound was prepared according to the procedure described in Example 1F, substituting the product of Example 52A for the product of Example 1E and substituting 6-methoxypyridine-3-boronic acid for pyrimidine-5-boronic acid. 1H NMR (300 MHz, CDCl3) δ ppm 8.00 (d, J=8.48 Hz, 1H) 7.87 (d, J=1.70 Hz, 1H) 7.68 (dd, J=9.16, 2.71 Hz, 1H) 7.49 (dd, J=8.48, 1.70 Hz, 1H) 7.39-7.44 (m, 1H) 6.70 (d, J=9.49 Hz, 1H) 3.75-3.88 (m, 1H) 3.65 (s, 3H) 3.56-3.63 (m, 1H) 3.00-3.16 (m, 1H) 2.66-2.80 (m, 2H) 2.52-2.65 (m, 2H) 2.18 (s, 3H) 1.05 (d, J=6.44 Hz, 6H). MS: (M+H)+=368.

Sources & evidence

ORD record
ord-194b376cd6b7455d8679f4386be94621
Source dataset
uspto-grants-2009_08
Patent number
US07576110B2

Reaction notes

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