Cesium carbonate → (2-Methyl-7-pyridin-3-yl-thiazolo[4,5-c]pyridin-4-yl)-(2-methyl-thiazol-4-yl)-amine

HRID 1443084Notes

Reaction equation

Cl[C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[S:10][C:6]=2[C:5]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:4][N:3]=1.[NH2:18][C:19]1[N:20]=[C:21]([CH3:24])[S:22][CH:23]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:11][C:9]1[S:10][C:6]2[C:5]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)=[CH:4][N:3]=[C:2]([NH:18][C:19]3[N:20]=[C:21]([CH3:24])[S:22][CH:23]=3)[C:7]=2[N:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-Chloro-2-methyl-7-pyridin-3-yl-thiazolo[4,5-c]pyridine (100 mg, 0.38 mmol) and 4-amino-2-methylthiazole (44 mg, 0.38 mmol) (Example C) were dissolved in 3 ml dry dioxane. 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (44 mg, 0.08 mmol) and cesium carbonate (200 mg, 0.61 mmol) were added and this mixture was evacuated and backfilled with argon several times to remove oxygen from the solution. Tris(dibenzylideneacetone)dipalladium chloroform complex (38 mg, 0.035 mmol) was added and the reaction mixture was stirred for 1 hour at 100° C. The reaction mixture was then evaporated and purified by flash chromatography on silica gel (heptane/ethyl acetate 90:10->0:100 gradient) and recrystallization in diisopropylether. The desired product was obtained as a yellow solid (20 mg, 15%), MS: m/e 354.1 (M+H+).

Workup

customthis mixture was evacuated
customto remove oxygen from the solution
additionTris(dibenzylideneacetone)dipalladium chloroform complex (38 mg, 0.035 mmol) was added
customThe reaction mixture was then evaporated
custompurified by flash chromatography on silica gel (heptane/ethyl acetate 90:10->0:100 gradient) and recrystallization in diisopropylether

Sources & evidence

ORD record: ord-e27c29bee49b45af9edf22c6e14e31cf
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659401B2

Reaction notes

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