4-Bromophenol → 4-(2-(4-Bromophenoxy)ethyl)morpholine

HRID 1875512Notes

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](C3C=CC(CC(NCC4C=CC=CC=4)=O)=NC=3)=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.ClCCN1CCOCC1.[Br:42]C1C=CC(O)=CC=1>>[Br:42][C:13]1[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:11][CH:12]=1

Participants

Reactant 3

HCID 78084-Bromophenol

HCID 767274-(2-Chloroethyl)morpholine

HCID 23635314Tirbanibulin

Product 1

HCID 20538154-(2-(4-Bromophenoxy)ethyl)morpholine

Procedure

In one aspect, the invention relates to a process for preparing 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide comprising the steps of: 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; 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; and (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.

Sources & evidence

ORD record: ord-e883d4c1691f49c5b18821f719a78c5d
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309549B2

Reaction notes

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