Dimethylformamide → N-Methyl-2-(6-methylaminopyridin-3-yl)benzothiazol-6-amine

HRID 1698112Notes

Reaction equation

Br[C:2]1[S:3][C:4]2[CH:10]=[C:9](O[Si](C(C)(C)C)(C)C)[CH:8]=[CH:7][C:5]=2[N:6]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[CH:29][C:30]([NH2:33])=[N:31][CH:32]=2)O1.C(=O)([O-])[O-].[K+].[K+].[CH2:41](Cl)Cl.[CH3:44][N:45](C=O)C>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]>[CH3:44][NH:45][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([C:27]3[CH:32]=[N:31][C:30]([NH:33][CH3:41])=[CH:29][CH:28]=3)[S:3][C:4]=2[CH:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-bromo-6-{[tert-butyl(dimethyl)silyl]oxy}-1,3-benzothiazole (500 mg, 1.45 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (383 mg, 1.2 equiv), aqueous potassium carbonate (2.0 M, 2.9 ml, 4.0 equiv) and Pd(dppf)Cl2 (119 mg, 0.10 equiv) in DMF (6.0 ml) was stirred at 80° C. under argon for 2 h. The mixture was then added to DCM (100 ml), dried (Na2SO4) and concentrated in vacuo. The crude thus obtained was purified by silica gel chromatography by gradient elution (n-heptane:ethyl acetate) to yield 237 mg of the title compound. 1H NMR δ 9.74 (s, 1H) 8.53 (d, 1H) 7.94 (dd, 1H) 7.73 (d, 1H) 7.35 (d, 1H) 6.93 (dd, 1H) 6.61 (s, 2H) 6.55 (d, 1H); MS m/z (M+H) 244.

Workup

dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe crude thus obtained
customwas purified by silica gel chromatography by gradient elution (n-heptane:ethyl acetate)

Sources & evidence

ORD record: ord-561dd0d8f338496d94b226926c3c9b4a
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163928B2

Reaction notes

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