Cesium carbonate → HCID 67537411, compound

HRID 1496631Notes

Reaction equation

Br[C:2]1[S:6][C:5]([CH2:7][CH3:8])=[N:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1.[CH3:16][C:17]1[CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:20]=[CH:19][N:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[CH2:7]([C:5]1[S:6][C:2]([C:21]2[CH:20]=[CH:19][N:18]=[C:17]([CH3:16])[CH:22]=2)=[C:3]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[N:4]=1)[CH3:8]

Participants

Conditions

Temperature: 90 °C

Procedure

In a microwave reactor, 100 mg (0.35 mmol) of 5-bromo-2-ethyl-4-(4-fluorophenyl)-1,3-thiazole, 100 mg (0.45 mmol) of 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, 1 ml of a 1M caesium carbonate solution and 28.7 mg (0.04 mmol) of [1,1′-bis(diphenylphosphino)-ferrocene/palladium(II) dichloride dichloromethane complex] in 2.5 ml of THF are, under argon, heated at 90° C. for 25 min. The reaction mixture is then filtered, the filter cake is washed with ethyl acetate (3×5 ml) and the combined filtrate is concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (cyclohexane/ethyl acetate). This gives 35 mg (24%) of the desired product; 1H-NMR(MeCN-d3) δ: 8.34 (d, 1H), 7.47 (m, 3H), 7.12 (s, 1H), 7.07 (m, 2H), 6.99 (d, 1H), 3.03 (q, 2H), 2.42 (s, 3H), 1.38 (t, 3H).

Workup

filtrationThe reaction mixture is then filtered
washthe filter cake is washed with ethyl acetate (3×5 ml)
concentrationthe combined filtrate is concentrated under reduced pressure
customThe residue is purified by column chromatography on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record: ord-2dcfe03d20514ba5b8117484e1823f2a
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09198426B2

Reaction notes

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