Sodium Carbonate → 3-chloro-6-(2-methoxyphenyl)-2-(4-trifluoromethylphenyl)-2H-indazole

HRID 270688Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)[C:6]=2[Cl:21].[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C1(P([Pd-3](Cl)(Cl)(P(C2C=CC=CC=2)C2C=CC=CC=2)[C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2].O1CCOCC1>[Cl:21][C:6]1[N:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[N:8]=[C:9]2[C:5]=1[CH:4]=[CH:3][C:2]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[O:23][CH3:22])=[CH:10]2

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of the product of Example 1 Step 3 (100 mg, 0.26 mmol), 2-methoxyphenylboronic acid (50 mg, 0.33 mmol), bis(diphenylphosphino)ferrocenyl palladium(II) dichloride 0) (20 mg), saturated Na2CO3 solution (1 mL) and dioxane (2 mL) was heated at 160° C. for 10 min via microwave irradiation. The title product was then purified by preparative thin layer chromatography on silica eluting with EtAc:hexanes 1:5. MS: (ES (M+1)) 403,405.

Workup

customThe title product was then purified by preparative thin layer chromatography on silica eluting with EtAc

Sources & evidence

ORD record: ord-833e758d4a1b4dc8adbc2c84843ddc42
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449585B2

Reaction notes

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