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

HRID 531486Notes

Reaction equation

HRID 531486 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=3)[CH:9]=2)[N:4]([S:22]([C:25]2[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:3]=1.CC1(C)C(C)(C)OB([C:40]2[CH:41]=[N:42][N:43]([CH2:45][C:46]3[CH:47]=[C:48]([CH:51]=[CH:52][CH:53]=3)[C:49]#[N:50])[CH:44]=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].COCCOC.O>[C:49]([C:48]1[CH:47]=[C:46]([CH:53]=[CH:52][CH:51]=1)[CH2:45][N:43]1[CH:44]=[C:40]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:12]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=4)[CH:9]=3)[N:4]([S:22]([C:25]3[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[CH:3]=2)[CH:41]=[N:42]1)#[N:50]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 710927463-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)benzonitrile2×HCID 90030209N-(3-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide2×

Product 1

HCID 90031340N-(3-(3-(1-(3-cyanobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methane sulfonamideYield 41.3%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-1, N-(3-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide (Intermediate 9) (200 mg, 0.35 mmol) was coupled with 3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)benzonitrile (Intermediate 14) (119.8 mg, 0.38 mmol) in sodium carbonate (111 mg, 1.05 mmol), PdCl2(dppf) (12.8 mg, 0.017 mmol) and DME/water (2/1 ml) to afford 90 mg (30% yield) of the pure product after column purification using 50% ethyl acetate in hexane as eluent.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-f955b314fcd34dcea77a0f758a6eca07
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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