Tri(butyl)vinyltin → 6-Ethenyl-1-(3-fluoro-4-hydroxyphenyl)-1H-indazol-4-ol

HRID 2423100Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([OH:19])[C:5]2[CH:6]=[N:7][N:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:18])[CH:12]=3)[C:9]=2[CH:10]=1.[CH2:20](C([Sn])=C(CCCC)CCCC)[CH2:21]CC>C(COC)OC>[CH:20]([C:2]1[CH:3]=[C:4]([OH:19])[C:5]2[CH:6]=[N:7][N:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:18])[CH:12]=3)[C:9]=2[CH:10]=1)=[CH2:21]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 6-bromo-1-(3-fluoro-4-hydroxyphenyl)-1H-indazol-4-ol (360 mg, 1.11 mmol) (E5) in dimethoxyethane (10 mL) was added dichlorobis(tris-o-tolylphosphine)palladium (44 mg, 0.056 mmol) and tributylvinyltin (0.65 mL, 2.22 mmol). The reaction mixture was heated at 90° C. under argon overnight. After cooling to room temperature, the mixture was filtered through a pad of celite. The filtrate was concentrated and the crude product purified by silica gel chromatography eluting with 5-100% ethyl acetate in hexane. The product was further purified by MDAP to yield the title compound (E6) (101 mg).

Workup

temperatureAfter cooling to room temperature
filtrationthe mixture was filtered through a pad of celite
concentrationThe filtrate was concentrated
customthe crude product purified by silica gel chromatography
washeluting with 5-100% ethyl acetate in hexane
customThe product was further purified by MDAP

Sources & evidence

ORD record: ord-51d5c66a897c4acca27f510e5c09f029
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960563B2

Reaction notes

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