2-Fluoropyridine → HCID 70974757, compound

HRID 1477218Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[N:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)=[CH:10][CH:11]=2)[C:6]1=[O:26].C([O-])([O-])=O.[Cs+].[Cs+].F[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1>>[N:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[O:1][CH2:2][CH2:3][CH2:4][N:5]1[N:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([C:15]3[CH:16]=[CH:17][C:18]([O:21][C:22]([F:25])([F:23])[F:24])=[CH:19][CH:20]=3)=[CH:10][CH:11]=2)[C:6]1=[O:26]

Participants

Reactant 3

HCID 97462-Fluoropyridine

HCID 10796Cesium carbonate

HCID 70974730HCID 70974730, compound

Product 1

HCID 70974757HCID 70974757, compound

Conditions

Temperature: 155 °C

Procedure

A mixture of 2-(3-hydroxypropyl)-7-(4-(trifluoromethoxy)phenyl)phthalazin-1(2H)-one (25 mg, 0.069 mmol), Cs2CO3 (67 mg, 0.21 mmol) and 2-fluoropyridine (100 μL) was heated to 155° C. overnight. The reaction was concentrated and purified by reverse phase HPLC to afford 2-(3-(pyridin-2-yloxy)propyl)-7-(4-(trifluoromethoxy)phenyl)phthalazin-1(2H)-one as a white solid. C23H18F3N3O3. 441.9 (M+1).

Workup

concentrationThe reaction was concentrated
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-d9b139bdc55d42139c4e297a2ef01ddf
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403782B2

Reaction notes

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