Water → 3-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)aniline

HRID 1400886Notes

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+].Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]2[CH:23]=[C:24]([I:26])[S:25][C:18]=12.O>CS(C)=O>[F:9][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[O:8][C:17]1[CH:22]=[CH:21][N:20]=[C:19]2[CH:23]=[C:24]([I:26])[S:25][C:18]=12)[NH2:1]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-amino-2-fluorophenol (1.83 g, 14.38 mmol) in DMSO (30 mL) was added potassium tert-butoxide (1.61 g, 14.38 mmol). After 15 min, 7-chloro-2-iodothieno[3,2-b]pyridine (2.5 g, 8.46 mmol, Ragan J. A. et al, Organic Process Research and Development, 2003, 7. 676-683) was added and the reaction mixture was heated at 100° C. for 60 min. The mixture was cooled down to RT then poured into water (250 mL) at 40-45° C. and stirred for 30 min. The precipitate was collected by filtration, washed with water, dried and purified by flash column chromatography on silica gel (eluent 60% EtOAc in Hexane) to afford title compound 268 (1.06 g, 32% yield) as a brown solid. 1H NMR (300 MHz, CDCl3) δ (ppm): 8.41 (d, J=5.4 Hz, 1H), 7.75 (s, 1H), 7.03 (t, J=9.0 Hz, 1H), 6.57-6.45 (m, 3H), 3.83 (s, 2H).

Workup

addition676-683) was added
temperatureThe mixture was cooled down to RT
filtrationThe precipitate was collected by filtration
washwashed with water
customdried
custompurified by flash column chromatography on silica gel (eluent 60% EtOAc in Hexane)

Sources & evidence

ORD record: ord-63a7ac1ff39943069b6ce31d689c984f
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906852B2

Reaction notes

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