Sodium Carbonate → N-[6-(2,3-diaminophenyl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide

HRID 1695797Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([NH:11][C:12]([C:14]2[N:15]=[C:16]([CH3:19])[S:17][CH:18]=2)=[O:13])[CH:3]=1.CC1(C)C(C)(C)OB([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([NH2:34])[C:29]=2[NH2:35])O1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C(Cl)Cl.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].O>[NH2:34][C:30]1[C:29]([NH2:35])=[CH:28][CH:33]=[CH:32][C:31]=1[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([NH:11][C:12]([C:14]2[N:15]=[C:16]([CH3:19])[S:17][CH:18]=2)=[O:13])[CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

N-(6-Bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide (200 mg,), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-benzenediamine (167 mg) (which may be prepared as described in WO2006005915), Pd(dppf)Cl2 (43 mg) and sodium carbonate (890 μl) were added to a microwave vial followed by 1,4-dioxane (2 ml) and water (2 ml). The mixture was heated under microwave irradiation at 150° C. for 15 min. The reaction was diluted with DCM (30 ml) and the layers separated. The aqueous layer was extracted further with DCM (2×30 ml) and the combined organic extracts were evaporated to dryness to give the title compound (250 mg).

Workup

customthe layers separated
extractionThe aqueous layer was extracted further with DCM (2×30 ml)
customthe combined organic extracts were evaporated to dryness

Sources & evidence

ORD record: ord-ef0cabcffc86481f8efcd62c65e7f95d
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163743B2

Reaction notes

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