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

HRID 531509Notes

Reaction equation

HRID 531509 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.[CH2:36]([O:43][CH2:44][CH2:45][O:46][C:47]1[CH:52]=[CH:51][C:50](B2OC(C)(C)C(C)(C)O2)=[CH:49][C:48]=1[NH:62][S:63]([CH3:66])(=[O:65])=[O:64])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O>[CH2:36]([O:43][CH2:44][CH2:45][O:46][C:47]1[CH:52]=[CH:51][C:50]([C:2]2[CH:3]=[C:4]3[C:10]([C:11]4[C:12]([CH3:25])=[N:13][N:14]([CH2:17][C:18]5[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=5)[C:15]=4[CH3:16])=[CH:9][N:8]([S:26]([C:29]4[CH:30]=[CH:31][C:32]([CH3:33])=[CH:34][CH:35]=4)(=[O:27])=[O:28])[C:5]3=[N:6][CH:7]=2)=[CH:49][C:48]=1[NH:62][S:63]([CH3:66])(=[O:64])=[O:65])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 90023451N-(2-(2-(benzyloxy)ethoxy)-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 90034098N-(2-(2-(benzyloxy)ethoxy)-5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methane sulfonamideYield 55.8%

Reagents, catalysts & solvents 1

HCID 86587398Ethanol toluene waterSolvent

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 (compound of step-i of example-14) (150 mg, 0.271 mmol) was coupled with N-(2-(2-(benzyloxy)ethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (intermediate 28) (242 mg, 0.542 mmol) in sodium carbonate (86 mg, 0.813 mmol) Pd(PPh3)2Cl2 (10 mg, 0.0135 mmol), Toluene/ethanol/water (5/2.5/1 ml) to afford 120 mg (55.8% yield) of the titled compound after purification by column (SiO2-eluted by 30% EA in hexanes). MS: m/z=794.1 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-368111ede11749a3bdf4c65ab455d508
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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