Sodium Carbonate → N-(3-(3-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide

HRID 531470Notes

Reaction equation

HRID 531470 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)[CH:15]=3)=[CH:9][N:8]([S:25]([C:28]3[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:5]2=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:43]2[CH:44]=[C:45]([NH:49][S:50]([CH3:53])(=[O:52])=[O:51])[CH:46]=[CH:47][CH:48]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1.C(O)C.O>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][N:14]2[CH:15]=[C:11]([C:10]3[C:4]4[C:5](=[N:6][CH:7]=[C:2]([C:43]5[CH:44]=[C:45]([NH:49][S:50]([CH3:53])(=[O:51])=[O:52])[CH:46]=[CH:47][CH:48]=5)[CH:3]=4)[N:8]([S:25]([C:28]4[CH:29]=[CH:30][C:31]([CH3:32])=[CH:33][CH:34]=4)(=[O:27])=[O:26])[CH:9]=3)[CH:12]=[N:13]2)=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 162177153-(Methanesulfonylamino)phenylboronic acid pinacol ester2×HCID 1185239695-bromo-3-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 118523966N-(3-(3-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamideYield 90.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-1, 5-bromo-3-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (240 mg, 0.44 mmol) was coupled with N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl) methane sulfonamide (intermediate 3) (160 mg, 0.53 mmol) in sodium carbonate (142 mg, 1.34 mmol), bis(triphenyl phosphine)palladium(ii) dichloride (16 mg, 0.022 mmol) and toluene/ethanol/water (7/7/4 ml) to afford 250 mg (89.28% yield) of the pure product after column purification using 35% ethyl acetate in hexane as eluent. MS: m/z=628.3 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-ccda166f3e32478ba64e0348df9c4302
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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