2-(Bromomethyl)-6-chloro-pyridine → trans-6-(6-Chloro-2-pyridyl)methoxy-3-(3-pyridyl)methyl-4-chromanol

HRID 610378Notes

Reaction equation

HRID 610378 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C@H:8]2[C@H:17]([OH:18])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=3)[O:10][CH2:9]2)[CH:2]=1.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27]Br)[N:22]=1>>[Cl:20][C:21]1[N:22]=[C:23]([CH2:27][O:19][C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[O:10][CH2:9][C@@H:8]([CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C@@H:17]3[OH:18])[CH:24]=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 220327372-(Bromomethyl)-6-chloro-pyridineHCID 67591831trans-3-(3-Pyridyl)methyl-4,6-chromandiol

Product 1

HCID 86754916trans-6-(6-Chloro-2-pyridyl)methoxy-3-(3-pyridyl)methyl-4-chromanol

Procedure

By the method of Example 5, 500 mg (1.95 mmol) of trans-3-(3-pyridyl)methyl-4,6-chromandiol and 442 mg (2.14 mmol) of 2-chloro-6-(bromomethyl)pyridine were converted to present title product, purified by flash chromatography on a silica gel column using isopropyl alcohol:ethyl acetate:CH2Cl2, 1:2:17 as eluant, to yield 0.11 g (14%) of present title compound as a glass.

Sources & evidence

ORD record
ord-7ab2604cf6724e2e976463c613f45b9d
Source dataset
uspto-grants-1999_12
Patent number
US05998451

Reaction notes

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