Potassium Carbonate → HCID 66942232, compound

HRID 1360811Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1B(O)O.[CH3:14][C:15]([NH:22][S:23]([C:26]1[CH:27]=[N:28][C:29](Cl)=[CH:30][CH:31]=1)(=[O:25])=[O:24])([CH3:21])[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:21][C:15]([NH:22][S:23]([C:26]1[CH:27]=[N:28][C:29]([C:4]2[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=2[O:9][CH3:10])=[CH:30][CH:31]=1)(=[O:25])=[O:24])([CH3:14])[CH2:16][C:17]([CH3:18])([CH3:19])[CH3:20]

Participants

Conditions

Temperature: 90 °C

Procedure

2,6-dimethoxyphenylboronic acid (1.0 g, 5.5 mmol), 6-Chloro-pyridine-3-sulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (555 mg, 1.8 mmol) and potassium carbonate (1.0 g, 7.3 mmol) were added to a degassed solution of tetrakis(triphenylphosphine) palladium (404 mg, 0.35 mmol) in toluol (12 ml) and ethanol (6 ml) and heated in a microwave reactor for 90 minutes at 90° C. The mixture was evaporated to dryness, suspended in 50 methanol and filtered off. The filtrate was evaporated to dryness and the residue was purified by flash chromatography (SiO2, heptane-ethyl acetate gradient) to return 639 mg of the title compound as an off-white solid, m/z=407 (ES+), 405 (ES−).

Workup

customThe mixture was evaporated to dryness
filtrationfiltered off
customThe filtrate was evaporated to dryness
customthe residue was purified by flash chromatography (SiO2, heptane-ethyl acetate gradient)

Sources & evidence

ORD record: ord-6d25677c25584c7d8c41b8b54a9c7679
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879884B2

Reaction notes

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