Dichloromethane → HCID 86660361, compound

HRID 1749353Notes

Reaction equation

HRID 1749353 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](C2C=CN=C(Cl)C=2)[CH:5]=[C:4]([Cl:15])[C:3]=1[S:16]([NH:19][C:20]1[C:21]([CH3:27])=[N:22][N:23]([CH3:26])[C:24]=1[CH3:25])(=[O:18])=[O:17].[CH:28]([C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1)=[O:29].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl>O=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:26][N:23]1[C:24]([CH3:25])=[C:20]([NH:19][S:16]([C:3]2[C:4]([Cl:15])=[CH:5][C:6]([C:32]3[CH:33]=[CH:34][CH:35]=[C:30]([CH:28]=[O:29])[CH:31]=3)=[CH:7][C:2]=2[Cl:1])(=[O:18])=[O:17])[C:21]([CH3:27])=[N:22]1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 27343563-Formylphenylboronic acidHCID 58561278HCID 58561278, compound

Product 1

HCID 86660361HCID 86660361, compoundYield 82.3%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 977OxygenSolvent

Procedure

Prepared from the sulphonamide of intermediate 2 (1.0 g, 2.43 mmol), 3-formylphenylboronic acid (440 mg, 2.91 mmol), tribasic potassium phosphate (620 mg, 2.91 mmol), Pd(dppf)Cl2.DCM (100 mg, 0.12 mmol) and water (0.5 ml) in oxygen-free DMF (6.0 ml) at 130° C. for 1 h according to the method of intermediate 11, to give the title compound as a white solid (870 mg, 2.0 mmol, 82%). δ H (D-6 DMSO, 300K) 10.12 (1H, s), 9.68 (1H, s), 8.42 (1H, s), 8.21 (1H, d J 7.9 Hz), 8.07 (2H, s), 8.01 (1H, d J 7.5 Hz), 7.74 (1H dd J 7.5 Hz 7.9 Hz), 3.58 (3H, s), 1.50 (3H, s), 1.75 (3H, s). m/z (ES+, 70V) 439.2 (MH+).

Sources & evidence

ORD record
ord-e1adca6f13064fe5b30e82708ceca8d7
Source dataset
uspto-grants-2015_10
Patent number
US09156811B2

Reaction notes

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