4-Bromo-2-methoxypyridine → HCID 57950267, compound

HRID 1918480Notes

Reaction equation

HRID 1918480 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][N:3]=1.Br[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([O:24][CH3:25])[CH:19]=1>>[CH3:25][O:24][C:20]1[CH:19]=[C:18]([C:5]2[CH:4]=[N:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[CH:23]=[CH:22][N:21]=1

Participants

3

Reactant 2

HCID 140623094-Bromo-2-methoxypyridineHCID 164142722-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Product 1

HCID 57950267HCID 57950267, compoundYield 98%

Procedure

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (3.5 g, 16 mmol) and 4-bromo-2-methoxypyridine (2.0 g, 11 mmol) were reacted according to Example 6 (step a) to provide the title compound (2.1 g, 98%) as a brown solid: 1H NMR (300 MHz, CDCl3) δ 8.75 (d, J=2.1 Hz, 1H), 8.23 (d, J=5.4 Hz, 1H), 7.78 (dd, J=8.0, 2.4 Hz, 1H), 7.24 (d, J=8.1, 1H), 7.08 (dd, J=5.4, 1.5 Hz, 1H), 6.84 (d, J=1.0, 1H), 3.98 (s, 3H), 2.61 (s, 3H).

Sources & evidence

ORD record
ord-5c5d7b234bc34d03b1fee8b9946891b2
Source dataset
uspto-grants-2013_12
Patent number
US08618299B2

Reaction notes

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