Water → 4-(2-(6-(1,3-Dioxan-2-yl)pyridin-3-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroaniline

HRID 1400898Notes

Reaction equation

Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([F:10])[CH:4]=1.CC([O-])(C)C.[K+].[O:17]1[CH2:22][CH2:21][CH2:20][O:19][CH:18]1[C:23]1[N:28]=[CH:27][C:26]([C:29]2[S:37][C:36]3[C:31](=[N:32][CH:33]=[CH:34][C:35]=3Cl)[CH:30]=2)=[CH:25][CH:24]=1.O>CS(C)=O>[O:17]1[CH2:22][CH2:21][CH2:20][O:19][CH:18]1[C:23]1[N:28]=[CH:27][C:26]([C:29]2[S:37][C:36]3[C:31](=[N:32][CH:33]=[CH:34][C:35]=3[O:9][C:6]3[CH:7]=[CH:8][C:3]([NH2:2])=[CH:4][C:5]=3[F:10])[CH:30]=2)=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 4-amino-2-fluorophenol hydrochloride (5.79 g, 35.4 mmol) in DMSO (40 mL) was added t-BuOK (8.66 g, 77.0 mmol). After 30 min, chloride 279 (10.70 g, 32.2 mmol) was added and the reaction mixture was heated at 100° C. for 1.5 h. More solution of 4-amino-2-fluorophenol HCl (860 mg, 7.70 mmol) and t-BuOK (0.86 g, 7.70 mmol) in DMSO (4 mL) was added to the reaction mixture that was heated at 100° C. for an additional 15 min. The reaction mixture was then poured into water (300 mL) to form a precipitate that was collected by filtration, dried under vacuum and triturated with MTBE to afford the title compound 280 (12.39 g, 29.3 mmol, 91% yield) as a beige solid. MS (m/z): 424.39 (M+H).

Workup

temperaturewas heated at 100° C. for an additional 15 min
customto form a precipitate that
filtrationwas collected by filtration
customdried under vacuum
customtriturated with MTBE

Sources & evidence

ORD record: ord-5e76504d7a354478b16bd02d63104e1e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906852B2

Reaction notes

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