Dichloromethane → US9156811, Ddd86206

HRID 1749366Notes

Reaction equation

HRID 1749366 reaction equation
C[N:2]([C:20]1[C:21]([CH3:27])=[N:22][N:23]([CH3:26])[C:24]=1[CH3:25])[S:3]([C:6]1[CH:11]=[CH:10][C:9](C2C=CC=C(C=O)C=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4].[N:28]1([C:34]2[CH:39]=[C:38](B3OC(C)(C)C(C)(C)O3)[CH:37]=[CH:36][N:35]=2)[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(Cl)[Cl:58]>CN(C=O)C.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]>[Cl:58][C:11]1[CH:10]=[C:9]([C:38]2[CH:37]=[CH:36][N:35]=[C:34]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH:39]=2)[CH:8]=[CH:7][C:6]=1[S:3]([NH:2][C:20]1[C:21]([CH3:27])=[N:22][N:23]([CH3:26])[C:24]=1[CH3:25])(=[O:4])=[O:5]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 162179482-(1-Piperaziny) pyridine-4-boronic acid pinacol esterHCID 907170953'-Formyl-biphenyl-4-sulfonic acid methyl-(1,3,5-trimethyl-1h-pyrazol-4-yl)-amide

Product 1

HCID 46179031US9156811, Ddd86206Yield 1,483.3%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Prepared from the sulphonamide of intermediate 3 (500 mg, 1.3 mmol), 2-(1-piperazinyl)pyridine-4-boronic acid pinacol ester (580 mg, 2.0 mmol), tribasic potassium phosphate (427 mg, 2.0 mmol), and Pd(dppf)Cl2.DCM (50 mg, 0.06 mmol) in DMF (3.0 ml) and water (0.75 ml), according to the method of intermediate 11, to give the title compound as an off-white powder (412 mg, 0.89 mmol, 68%). δH (D-6 DMSO, 300K) 8.20 (1H, d J 5.2 Hz), 8.14 (1H, d J 1.7 Hz), 7.84 (1H, dd J 1.75 Hz 8.3 Hz), 7.79 (1H, d J 8.3 Hz), 7.13 (1H, s), 6.99 (1H, dd J 1.15 Hz 5.2 Hz), 3.55 (3H, s), 3.51 (4H, s br), 2.79 (4H, s br), 1.90 (3H, s), 1.69 (3H, s). m/z (ES+, 70V) 461.2 (MH+).

Sources & evidence

ORD record
ord-ec606811be354cb7b0843fad1267b6c3
Source dataset
uspto-grants-2015_10
Patent number
US09156811B2

Reaction notes

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