Sodium Carbonate → HCID 58255738, compound

HRID 1695760Notes

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.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1.CC1(C)C(C)(C)OB([C:40]2[CH:41]=[C:42]([CH2:46][S:47]([NH2:50])(=[O:49])=[O:48])[CH:43]=[CH:44][CH:45]=2)O1>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>[NH2:50][S:47]([CH2:46][C:42]1[CH:43]=[C:44]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[N:7][NH:8]3)=[C:4]([NH:11][C:12]([C:14]3[N:15]=[C:16]([CH3:19])[S:17][CH:18]=3)=[O:13])[CH:3]=2)[CH:45]=[CH:40][CH:41]=1)(=[O:48])=[O:49]

Participants

Conditions

Temperature: 150 °C

Procedure

N-(6-Bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide (50 mg, 0.148 mmol), Pd(dppf)Cl2 (12 mg, 0.015 mmol), 2 M sodium carbonate (aq) (0.222 ml, 0.444 mmol), 1,4-dioxane (1 ml) and water (1 ml) were added to 1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonamide (53 mg, 0.178 mmol). The reaction was heated in a Biotage microwave at 150° C. for 15 mins. The reaction mixture was extracted with DCM (2×20 ml) and the separated, combined organic layer was evaporated to dryness. The residue was dissolved in MeOH:DMSO (1 ml, 1:1, v/v) and purified by MDAP (Method B). Appropriate fractions were dried under a stream of nitrogen to give title compound, 5 mg.

Workup

extractionThe reaction mixture was extracted with DCM (2×20 ml)
customwas evaporated to dryness
dissolutionThe residue was dissolved in MeOH
customDMSO (1 ml, 1:1, v/v) and purified by MDAP (Method B)
customAppropriate fractions were dried under a stream of nitrogen

Sources & evidence

ORD record: ord-dd7eb1313d1143d38815f53985c19855
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163743B2

Reaction notes

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