Phenol, 4-amino-2-fluoro- → 4-(2-(5-(1,3-Dioxan-2-yl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroaniline

HRID 409966Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.CC(C)([O-])C.[K+].[O:16]1[CH2:21][CH2:20][CH2:19][O:18][CH:17]1[C:22]1[CH:23]=[CH:24][C:25]([C:28]2[S:36][C:35]3[C:30](=[N:31][CH:32]=[CH:33][C:34]=3Cl)[CH:29]=2)=[N:26][CH:27]=1>CS(C)=O.O>[O:16]1[CH2:21][CH2:20][CH2:19][O:18][CH:17]1[C:22]1[CH:23]=[CH:24][C:25]([C:28]2[S:36][C:35]3[C:30](=[N:31][CH:32]=[CH:33][C:34]=3[O:8][C:5]3[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][C:4]=3[F:9])[CH:29]=2)=[N:26][CH:27]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-amino-2-fluorophenol (7.42 g, 58.4 mmol) in DMSO (65 mL) was added potassium tert-butoxide (7.75 g, 69.0 mmol)). After 30 min, intermediate 317 (17.67 g, 53.1 mmol) was added and the reaction mixture was heated at 100° C. for 1.5 h, cooled down to room temperature, poured in water (300 mL) at 40-45° C. and stirred for 30 min. The solid was collected by filtration, washed with water (2×30 mL) and dried for 2 h. This material was triturated with ether (60 mL), to afford title compound 319 (19.80 g, 88% yield) as a brown solid. MS (m/z): 424.1 (M+H).

Workup

temperaturecooled down to room temperature
filtrationThe solid was collected by filtration
washwashed with water (2×30 mL)
customdried for 2 h
customThis material was triturated with ether (60 mL)

Sources & evidence

ORD record: ord-e0413f388fe14a4da90ac10f09c3ebde
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759522B2

Reaction notes

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