Potassium Carbonate → HCID 91586804, compound

HRID 857374Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:37])[CH2:4][CH:5]1[C:9]2=[C:10]([S:29][C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[C:11]3[C:12]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:13][C:14](OS(C(F)(F)F)(=O)=O)=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6]1.[Cl:38][C:39]1[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CCO.[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>[CH3:1][O:2][C:3](=[O:37])[CH2:4][CH:5]1[C:9]2=[C:10]([S:29][C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[C:11]3[C:12]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:13][C:14]([C:42]4[CH:43]=[CH:44][C:39]([Cl:38])=[CH:40][CH:41]=4)=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6]1

Participants

Conditions

Temperature: 80 °C

Procedure

To the compound of Step 2 (53 mg, 0.089 mmol) in toluene/EtOH 3:1 mixture (4 mL) was added 4-chlorophenylboronic acid (28 mg, 0.18 mmol), K2CO3 (18 mg, 0.13 mmol), and tetrakis (triphenylphosphine) palladium (0) (5.1 mg, 0.04 mmol). The reaction mixture was stirred at 80° C. overnight. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to provide the title compound (40 mg)

Workup

customThe reaction was quenched with saturated aqueous NH4Cl
extractionextracted with EtOAc
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-7c3346125d3d4509bab3866165b905e0
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144913B2

Reaction notes

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