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

HRID 531508Notes

Reaction equation

HRID 531508 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.[CH3:36][N:37]([CH3:61])[CH2:38][CH2:39][O:40][C:41]1[CH:46]=[CH:45][C:44](B2OC(C)(C)C(C)(C)O2)=[CH:43][C:42]=1NS(C)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.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:44]4[CH:45]=[CH:46][C:41]([O:40][CH2:39][CH2:38][N:37]([CH3:61])[CH3:36])=[CH:42][CH:43]=4)[CH:3]=3)[N:8]([S:26]([C:29]3[CH:30]=[CH:31][C:32]([CH3:33])=[CH:34][CH:35]=3)(=[O:28])=[O:27])[CH:9]=2)[C:12]([CH3:25])=[N:13]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 90030709N-(2-(2-(dimethylamino)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 1185240762-(4-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenoxy)-N,N-dimethylethanamineYield 45.3%

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 1 of Example 14) (100 mg, 0.18 mmol) was coupled with N-(2-(2-(dimethylamino)ethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methane sulfonamide (Intermediate 27) (229 mg, 0.596 mmol) in sodium carbonate (57 mg, 0.54 mmol) Pd(PPh3)2Cl2 (6 mg, 0.009 mmol), Toluene/ethanol/water (5/2.5/1 ml) to afford 52 mg (39.39% yield) of the titled compound after purification by preparative TLC (SiO2-eluted by 5% methanolic ammonia in DCM). MS: m/z=731.4 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-fdc379f725b9448f853824e2efa86bb6
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…