Sodium Carbonate → 5-(3-(1-(2,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy-N-methylbenzenesulfonamide

HRID 531504Notes

Reaction equation

HRID 531504 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([O:22][CH3:23])=[C:15]([S:17]([NH:20][CH3:21])(=[O:19])=[O:18])[CH:16]=3)[CH:9]=2)[N:4]([S:24]([C:27]2[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH:3]=1.[F:34][C:35]1[CH:57]=[CH:56][C:55]([F:58])=[CH:54][C:36]=1[CH2:37][N:38]1[C:42]([CH3:43])=[C:41](B2OC(C)(C)C(C)(C)O2)[C:40]([CH3:53])=[N:39]1.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>[F:34][C:35]1[CH:57]=[CH:56][C:55]([F:58])=[CH:54][C:36]=1[CH2:37][N:38]1[C:42]([CH3:43])=[C:41]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:12]=[CH:13][C:14]([O:22][CH3:23])=[C:15]([S:17]([NH:20][CH3:21])(=[O:19])=[O:18])[CH:16]=4)[CH:9]=3)[N:4]([S:24]([C:27]3[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH:3]=2)[C:40]([CH3:53])=[N:39]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 900300305-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy-N-methylbenzenesulfonamide2×HCID 900311871-[(2,5-Difluorophenyl)methyl]-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazole2×

Product 1

HCID 1185239145-(3-(1-(2,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy-N-methylbenzenesulfonamideYield 61.4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

Using similar reaction conditions as described in step-ii of example 15-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy-N-methylbenzenesulfonamide (intermediate 22) (200 mg, 0.335 mmol) was coupled with 1-(2,5-difluorobenzyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Intermediate 25) (146 mg, 0.418 mmol) in sodium carbonate (106 mg, 1.0 mmol), Pd(PPh3)2Cl2 (11.7 mg, 0.011 mmol), Toluene/ethanol/water (20/10/2 ml) to afford 142 mg (61.4% yield) of the titled compound after purification by column (SiO2-eluted by 0.4 to 1.2% MeOH in CHCl3). MS: m/z=692.1 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-421e2d873dc74f1cb6027572932ffcd7
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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