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

HRID 1875527Notes

Reaction equation

HRID 1875527 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[CH:18][C:19](CC(NCC4C=CC=CC=4)=O)=[N:20][CH:21]=3)=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.BrC1C=CC(OCCN2CCOCC2)=CC=1.B(O)(O)C1C=CC([F:56])=NC=1>>[F:56][C:19]1[N:20]=[CH:21][C:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:11][CH:12]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 20538154-(2-(4-Bromophenoxy)ethyl)morpholineHCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 23635314Tirbanibulin

Product 1

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

Procedure

In another aspect, the invention relates to the process for preparing 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide comprising the steps of 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; 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; converting 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetonitrile to methyl 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetate; and 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.

Sources & evidence

ORD record
ord-e004973f94924329ba54615569fcf165
Source dataset
uspto-grants-2012_11
Patent number
US08309549B2

Reaction notes

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