Phenylboronic Acid → HCID 11237417, compound

HRID 2374284Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:4][C:3]=1[C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)=[O:14].[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[F-].[K+]>O1CCOCC1.C(OCC)(=O)C.[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[CH3:12][NH:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:3]([C:13]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:30])[F:29])=[CH:25][CH:26]=3)[CH2:17][CH2:16]2)=[O:14])[CH:4]=1)(=[O:9])=[O:10]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-Chloro-N-methyl-3-[4-(4-trifluoromethyl-phenyl)-piperazine-1-carbonyl]-benzenesulfonamide (Example M; 30 mg, 0.065 mmol) in dioxane (2 ml) was added phenylboronic acid (12 mg, 0.098 mmol) followed by potassium fluoride (12 mg) and bis(tri-t-butylphosphine) palladium. The reaction mixture was then stirred for 19 hours at 90° C. After such time were added again (every 24 hours) the same amounts of phenylboronic acid, potassium fluoride, and bis(tri-t-butylphosphine) palladium After 3 days, the reaction mixture was diluted with ethyl acetate, filtered and concentrated in vacuo. The residue was purified by preparative HPLC (MeCN, H20+0.005 N HCOOH) to yield the title compound (7.4 mg). (M+H+: 504.4.)

Workup

filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by preparative HPLC (MeCN, H20+0.005 N HCOOH)

Sources & evidence

ORD record: ord-7913eb5e87224c589ff81c5fab346bd6
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462617B2

Reaction notes

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