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

HRID 531515Notes

Reaction equation

HRID 531515 reaction equation
FC1C=CC=CC=1CN1C=C(C2C3C(=NC=C(C4C=C(NS(C)(=O)=O)C=CC=4)C=3)NC=2)C=N1.Br[C:35]1[CH:36]=[C:37]2[C:43]([C:44]3[C:45]([CH3:58])=[N:46][N:47]([CH2:50][C:51]4[CH:56]=[CH:55][CH:54]=[C:53]([F:57])[CH:52]=4)[C:48]=3[CH3:49])=[CH:42][N:41]([S:59]([C:62]3[CH:68]=[CH:67][C:65]([CH3:66])=[CH:64][CH:63]=3)(=[O:61])=[O:60])[C:38]2=[N:39][CH:40]=1.[CH3:69][N:70]([CH3:95])[CH2:71][CH2:72][CH2:73][O:74][C:75]1[CH:80]=[CH:79][C:78](B2OC(C)(C)C(C)(C)O2)=[CH:77][C:76]=1[NH:90][S:91]([CH3:94])(=[O:93])=[O:92].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[CH3:95][N:70]([CH3:69])[CH2:71][CH2:72][CH2:73][O:74][C:75]1[CH:80]=[CH:79][C:78]([C:35]2[CH:36]=[C:37]3[C:43]([C:44]4[C:45]([CH3:58])=[N:46][N:47]([CH2:50][C:51]5[CH:56]=[CH:55][CH:54]=[C:53]([F:57])[CH:52]=5)[C:48]=4[CH3:49])=[CH:42][N:41]([S:59]([C:62]4[CH:63]=[CH:64][C:65]([CH3:66])=[CH:67][CH:68]=4)(=[O:60])=[O:61])[C:38]3=[N:39][CH:40]=2)=[CH:77][C:76]=1[NH:90][S:91]([CH3:94])(=[O:93])=[O:92]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 72944747N-(3-(3-(1-(2-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamideHCID 900313065-bromo-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 90031661N-(2-(3-(dimethylamino)propoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide

Product 1

HCID 90030630N-(2-(3-(dimethylamino)propoxy)-5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamideYield 13.4%

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

Using similar reaction conditions as described in step-ii of example 1, 5-bromo-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (step-i of example-14) (250 mg, 0.4 mmol) was coupled with N-(2-(3-(dimethylamino)propoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (intermediate-30) (200 mg, 0.5 mmol) in sodium carbonate (154 mg, 1.4 mmol) PdCl2(dppf) (18 mg, 0.05 mmol), 1,2-dimethoxyethane/water (2/2 mL) to afford 40 mg (12% yield) of the titled compound after purification by preparative TLC (SiO2)-eluted by 30% ethyl acetate in hexane.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-41aa28dadfdf47f68bbaa515dd809037
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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