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

HRID 531512Notes

Reaction equation

HRID 531512 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[C:12]([CH3:25])=[N:13][N:14]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=4)[C:15]=3[CH3:16])=[CH:9][N:8]([S:26]([C:29]3[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:5]2=[N:6][CH:7]=1.CO[C:38]1[CH:68]=[CH:67][C:41]([O:42][CH2:43][CH2:44][CH2:45][O:46][C:47]2[CH:52]=[CH:51][C:50](B3OC(C)(C)C(C)(C)O3)=[CH:49][C:48]=2[NH:62][S:63]([CH3:66])(=[O:65])=[O:64])=[CH:40][CH:39]=1.[C:69](=[O:72])([O-])[O-].[Na+].[Na+].[CH3:75]OCCOC.O>>[F:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][N:14]1[C:15]([CH3:16])=[C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([C:50]4[CH:51]=[CH:52][C:47]([O:46][CH2:45][CH2:44][CH2:43][O:42][CH2:41][C:40]5[CH:39]=[CH:38][C:68]([O:72][CH3:69])=[CH:67][CH:75]=5)=[C:48]([NH:62][S:63]([CH3:66])(=[O:64])=[O:65])[CH:49]=4)[CH:3]=3)[N:8]([S:26]([C:29]3[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=3)(=[O:27])=[O:28])[CH:9]=2)[C:12]([CH3:25])=[N:13]1

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 18180031Water 1,2-dimethoxyethaneHCID 90030701N-(2-(3-(4-methoxyphenoxyl)propoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide2×HCID 900313065-bromo-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 118523947N-(5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(3-((4-methoxybenzyl)oxy)prop oxy)phenyl)methanesulfonamideYield 41%

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) (200 mg, 0.3 mmol) was coupled with N-(2-(3-(4-methoxyphenoxyl)propoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (intermediate 29) (160 mg, 0.3 mmol) in sodium carbonate (120 mg, 1 mmol) PdCl2 (dppf) (14 mg, 0.001 mmol), 1,2-dimethoxy ethane/water (2/2 mL) to afford 120 mg (41% yield) of the titled compound after purification by column (SiO2-eluted by 30% EA in hexanes).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-145dd0a85c5d48e8a1b0ffae15357bea
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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