4-(2-(4-Bromophenoxy)ethyl)morpholine → 4-(2-(4-(6-Fluoropyridin-3-yl)phenoxy)ethyl)morpholine

HRID 1875516Notes

Reaction equation

HRID 1875516 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.B(O)(O)[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[N:20][CH:19]=1>>[F:24][C:21]1[N:20]=[CH:19][C:18]([C:2]2[CH:16]=[CH:15][C:5]([O:6][CH2:7][CH2:8][N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[CH:4][CH:3]=2)=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 20538154-(2-(4-Bromophenoxy)ethyl)morpholine2×HCID 2783397(6-Fluoropyridin-3-yl)boronic acid

Product 1

HCID 441854204-(2-(4-(6-Fluoropyridin-3-yl)phenoxy)ethyl)morpholine

Procedure

In another aspect the invention relates to a process for preparing 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide mesylate comprising the steps of: (1) reacting 4-(2-chloroethyl)morpholine with 4-bromophenol to yield 4-(2-(4-bromophenoxy)ethyl)morpholine; (2) coupling 4-(2-(4-bromophenoxy)ethyl)morpholine with 6-fluoropyridin-3-yl-3-boronic acid to yield 4-(2-(4-(6-fluoropyridin-3-yl)phenoxy)ethyl)morpholine; (3) reacting 4-(2-(4-(6-fluoropyridin-3-yl)phenoxy)ethyl)morpholine with acetonitrile to yield 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetonitrile; (4) converting 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetonitrile to methyl 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetate; (5) reacting methyl 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetate with benzylamine to yield 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide; and (6) contacting 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide with methane sulfonic acid to yield 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide mesylate.

Sources & evidence

ORD record
ord-a556b752c2cb4df39b0cc313ae5ba091
Source dataset
uspto-grants-2012_11
Patent number
US08309549B2

Reaction notes

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