Sodium Carbonate → HCID 90030421, compound

HRID 531488Notes

Reaction equation

HRID 531488 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19](Br)[CH:20]=3)[N:15]([S:23]([C:26]3[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:14]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:41]2[CH:42]=[C:43]([NH:47][S:48]([CH3:51])(=[O:50])=[O:49])[CH:44]=[CH:45][CH:46]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>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].C1(C)C=CC=CC=1.C(O)C.O>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:41]4[CH:42]=[C:43]([NH:47][S:48]([CH3:51])(=[O:49])=[O:50])[CH:44]=[CH:45][CH:46]=4)[CH:20]=3)[N:15]([S:23]([C:26]3[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:14]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 162177153-(Methanesulfonylamino)phenylboronic acid pinacol ester2×HCID 90030824HCID 90030824, compound

Product 1

HCID 90030421HCID 90030421, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-1, 3-(1-benzyl-1H-pyrazol-4-yl)-5-bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine (220 mg, 0.433 mmol) was coupled with N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (intermediate 3) in Sodium carbonate (137.68 mg, 1.29 mmol), PdCl2(dppf) (15.8 mg, 0.02 mmol), toluene/ethanol/water (5/5/2 ml). This on purification by preparative TLC using methanol/chloroform as eluent afforded 120 mg (46.3% yield) of the pure compound.

Workup

  1. customreaction conditions
  2. customThis on purification by preparative TLC

Sources & evidence

ORD record
ord-dc271df01d924edfa88d070ce8b6fe14
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…