Water → HCID 178507273, compound

HRID 1615989Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][NH:13]3)O1.Br[C:20]1[CH:21]=[C:22]([NH2:30])[C:23]2[C:24]([F:29])=[N:25][NH:26][C:27]=2[CH:28]=1.O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:29][C:24]1[C:23]2[C:22]([NH2:30])=[CH:21][C:20]([C:9]3[CH:17]=[CH:16][CH:15]=[C:14]4[C:10]=3[CH:11]=[CH:12][NH:13]4)=[CH:28][C:27]=2[NH:26][N:25]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (24 mg) and 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) (3 mg) at 20° C. in a microwave vial was added a solution of 6-bromo-3-fluoro-1H-indazol-4-amine (19 mg) in 1,4-dioxane (0.75 ml) followed by water (0.5 ml) and aqueous sodium carbonate (2M, 0.124 ml). The reaction vessel was sealed and heated under microwave irradiation at 150° C. for 15 min. After cooling, the black solution was loaded onto a 500 mg silica cartridge which was then eluted with methanol (4 column volumes). The eluant was blown to dryness, re-dissolved in methanol (3 ml), filtered and blown to dryness to give the title compound (67 mg) as a brown film.

Workup

customThe reaction vessel was sealed
temperatureAfter cooling
washwas then eluted with methanol (4 column volumes)
dissolutionre-dissolved in methanol (3 ml)
filtrationfiltered

Sources & evidence

ORD record: ord-a424bf5ff3684aabb2517c60ad4d2576
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765743B2

Reaction notes

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