2-Thiazolamine, 5-bromo- → 5-[1-Methyl-3-(trifluoromethyl)pyrazol-5-yl]-1,3-thiazole-2-ylamine

HRID 1524243Notes

Reaction equation

[CH3:1][N:2]1[C:6](B(O)O)=[CH:5][C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1.[NH2:14][C:15]1[S:16][C:17](Br)=[CH:18][N:19]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C.O1CCOCC1.O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[CH3:1][N:2]1[C:6]([C:17]2[S:16][C:15]([NH2:14])=[N:19][CH:18]=2)=[CH:5][C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of (1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)boronic acid (290 mg, 1.5 mmol), 2-amino-5-bromothiazole (1 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (A-Phos) (53 mg) and K3PO4 (212 mg, 1 mmol) in 2 ml ACN, 2 ml dioxane, 0.5 ml H2O was bubbled with argon before heated at 70° C. for 1 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine, dried over Na2SO4, concentrated to dryness. Prep HPLC purification furnished 4.6 mg 5-[1-methyl-3-(trifluoromethyl)pyrazol-5-yl]-1,3-thiazole-2-ylamine (63) as light yellow solid (yield 1.9%; purity>95%).

Workup

customwas bubbled with argon
temperatureAfter cooling down to r.t.
washwashed with aq. NaHCO3 and brine
dry with materialdried over Na2SO4
concentrationconcentrated to dryness
customPrep HPLC purification

Sources & evidence

ORD record: ord-bd185c6d38b746c3a0f2d3eadb7a87c0
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079891B2

Reaction notes

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