Water → 3-Fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)aniline

HRID 1676233Notes

Reaction equation

[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([F:11])[CH:5]=1.Cl[C:13]1[CH:18]=[CH:17][N:16]=[C:15]2[CH:19]=[CH:20][S:21][C:14]=12.O>CS(C)=O>[F:11][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[O:10][C:13]1[CH:18]=[CH:17][N:16]=[C:15]2[CH:19]=[CH:20][S:21][C:14]=12)[NH2:3]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred suspension of NaH (0.432 g, 18.0 mmol) in DMSO (30 mL) was carefully added 4-amino-2-fluorophenol (1.91 g, 15.0 mmol) in portions. The reaction was stirred under N2 for 15 minutes. 7-Chlorothieno[3,2-b]pyridine (2.54 g, 15.0 mmol) was added as a solid. The reaction was heated to 100° C. for 2 hours. The reaction was allowed to cool to room temperature, and water (40 mL) was carefully added. The suspension was filtered. The brown solid was washed with water (2×10 mL), and dried by toluene azeotrope (5×20 mL) by rotary evaporation at 50° C. The solid was recrystallized from hot toluene (10 mL) to obtain a brown, crystalline solid (2.64 g, 68%). 1H NMR (400 MHz, CDCl3) δ 8.49 (d, J=6 Hz, 1H), 7.73 (d, J=6 Hz, 1H), 7.56 (d, J=6 Hz, 1H), 7.04 (t, J=9 Hz, 1H), 6.51 (m, 3H), 3.83 (br s, 2H). LRMS (APCI pos) m/e 261 (M+1).

Workup

temperatureto cool to room temperature
filtrationThe suspension was filtered
washThe brown solid was washed with water (2×10 mL)
dry with materialdried by toluene azeotrope (5×20 mL) by rotary evaporation at 50° C
customThe solid was recrystallized from hot toluene (10 mL)

Sources & evidence

ORD record: ord-14d2ba859b6e4c458205641c480cfe17
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003662B2

Reaction notes

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