1,4-Dioxane → HCID 44539726, compound

HRID 1695809Notes

Reaction equation

[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([CH2:9][C:10]2[S:11][CH:12]=[C:13]([C:15]([NH:17][C:18]3[CH:26]=[C:25](B4OC(C)(C)CC(C)(C)O4)[CH:24]=[C:23]4[C:19]=3[CH:20]=[N:21][N:22]4[CH3:37])=[O:16])[N:14]=2)[CH2:3]1.Br[C:39]1[CH:40]=[C:41]([NH:46][S:47]([CH3:50])(=[O:49])=[O:48])[C:42]([Cl:45])=[N:43][CH:44]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].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].O>[Cl:45][C:42]1[N:43]=[CH:44][C:39]([C:25]2[CH:24]=[C:23]3[C:19]([CH:20]=[N:21][N:22]3[CH3:37])=[C:18]([NH:17][C:15]([C:13]3[N:14]=[C:10]([CH2:9][N:4]4[CH2:5][C@H:6]([CH3:8])[O:7][C@H:2]([CH3:1])[CH2:3]4)[S:11][CH:12]=3)=[O:16])[CH:26]=2)=[CH:40][C:41]=1[NH:46][S:47]([CH3:50])(=[O:49])=[O:48]

Participants

Conditions

Temperature: 100 °C

Procedure

2-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-N-[1-methyl-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide (50 mg), N-(5-bromo-2-chloro-3-pyridinyl)methanesulfonamide (27 mg), tripotassium phosphate (61 mg) and Pd(dppf)Cl2 (7 mg) were added to 1,4-dioxane (0.5 ml) and water (0.5 ml) and heated under microwave irradiation for 10 min at 100° C. The reaction was passed through a 2 g silica SPE cartridge, washing with MeOH then evaporating to dryness. The residue was purified on silica, eluting with 0-100% EtOAc/cyclohexane over 30 min to give the title compound (27 mg).

Workup

washwashing with MeOH
customthen evaporating to dryness
customThe residue was purified on silica
washeluting with 0-100% EtOAc/cyclohexane over 30 min

Sources & evidence

ORD record: ord-42bc976d7c744c168dce0c8bf55a4944
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163743B2

Reaction notes

Loading…