1,4-Dioxane → 3-Fluoro-4-(2-(furan-2-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine

HRID 1676288Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:16]=[C:17](I)[S:18][C:11]=12)[NH2:5].C([Sn](CCCC)(CCCC)[C:25]1[O:26][CH:27]=[CH:28][CH:29]=1)CCC.O1CCOCC1>[Cl-].[Na+].O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([NH2:5])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:16]=[C:17]([C:25]3[O:26][CH:27]=[CH:28][CH:29]=3)[S:18][C:11]=12

Participants

Conditions

Temperature: 90 °C

Procedure

A 100 mL, single-neck, round-bottomed flask was charged with 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)benzenamine (0.300 g, 0.7768 mmol) from Example 6, Step A, PdCl2(PPh3)2 (0.02726 g, 0.03884 mmol), tributyl(furan-2-yl)stannane (0.2931 ml, 0.9322 mmol), and dioxane (8 mL). Heat to 90° C. for 6 hours under nitrogen and cool to room temperature. The reaction mixture was diluted with brine (100 mL) and extracted with EtOAc (100 mL). The reaction mixture was purified by triturating with hot MeOH. The product (170 mg, 57%) was isolated as a brown solid. LRMS (APCI+) m/e 327 (M+1) detected.

Workup

temperaturecool to room temperature
extractionextracted with EtOAc (100 mL)
customThe reaction mixture was purified
customby triturating with hot MeOH

Sources & evidence

ORD record: ord-36956659f4e54101a59ac0869a419ea4
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003662B2

Reaction notes

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