Potassium Phosphate, Tribasic → HCID 58603980, compound

HRID 268595Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[CH3:9][S:10]([C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1)(=[O:12])=[O:11].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C>[CH3:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of 2-chloro-4-methylpyridine (3 g, 23.5 mmol), 4-(methylsulfonyl)phenylboronic acid (5.64 g, 28.2 mmol), potassium phosphate (12.0 g, 56.4 mmol) and DMF (50 mL) under an atmosphere of nitrogen was added palladium tetrakistriphenylphosphine (1.36 g, 1.18 mmol). After heating at 120° C. for 14 hours, the reaction was cooled and the DMF removed in vacuo. The residue was partitioned between ethyl acetate (100 mL) and water (100 mL), separated and the organic layer dried over sodium sulfate and concentrated in vacuo. Purification by silica chromatography eluting with a gradient of ethyl acetate in cyclohexane gave the title compound (4.29 g, 74%) TLC RF 0.19 (1:1 ethyl acetate:cyclohexane) LC retention time 2.36 mins, MS m/z 248 (MH+)

Workup

temperaturethe reaction was cooled
customthe DMF removed in vacuo
customThe residue was partitioned between ethyl acetate (100 mL) and water (100 mL)
customseparated
dry with materialthe organic layer dried over sodium sulfate
concentrationconcentrated in vacuo
customPurification by silica chromatography
washeluting with a gradient of ethyl acetate in cyclohexane

Sources & evidence

ORD record: ord-166115e1c4454c5e984fe8ddf1d2fc15
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446117B2

Reaction notes

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