Cesium carbonate → HCID 69671335, compound

HRID 1497566Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[N:9][N:10]=2)[CH:7]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:8]1[N:6]2[CH:7]=[C:2]([C:24]3[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=3)[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A flask was charged with 6-bromo-3-(2-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine (151 mg, 0.5 mmol), 4-methoxyphenylboronic acid (80 mg, 0.5 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 5.8 mg, 0.005 mmol), cesium carbonate (Cs2CO3, 326 mg, 1.0 mmol), 1,4-dioxane (10 mL) and water (2 mL). The mixture was stirred at 100° C. under Argon for 10 h. The mixture was evaporated to afford the crude product. The crude product was purified by column chromatography on silica gel (petroleum ether:ethyl acetate=1:1) to give the title compound (140 mg, 84.2% yield) as yellow solids. 1H NMR (DMSO-d6): 8.06 (m, 1H), 7.90 (dd, J=9.5 and 0.9 Hz, 1H), 7.75 (dd, J=9.6 and 1.8 Hz, 1H), 7.67-7.62 (m, 4H), 7.32 (d, J=8.1 Hz, 1H), 7.19 (t, J=7.5 Hz, 1H), 7.03 (d, J=8.7 Hz, 2H), 3.85 (s, 3H), 3.80 (s, 3H). MS: m/z 332.2 [M+H+].

Workup

customThe mixture was evaporated
customto afford the crude product
customThe crude product was purified by column chromatography on silica gel (petroleum ether:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-153eb772d33a4628b77518fec5bd2762
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199983B2

Reaction notes

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