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-morpholino phenyl)methanesulfonamide

HRID 531572Notes

Reaction equation

HRID 531572 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.[O:36]1[CH2:41][CH2:40][N:39]([C:42]2[CH:47]=[CH:46][C:45](B3OC(C)(C)C(C)(C)O3)=[CH:44][C:43]=2[NH:57][S:58]([CH3:61])(=[O:60])=[O:59])[CH2:38][CH2:37]1.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:45]4[CH:46]=[CH:47][C:42]([N:39]5[CH2:38][CH2:37][O:36][CH2:41][CH2:40]5)=[C:43]([NH:57][S:58]([CH3:61])(=[O:59])=[O:60])[CH:44]=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 900313065-bromo-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 90064794N-(2-Morpholino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)methanesulfonamide2×

Product 1

HCID 118524056N-(5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-morpholino phenyl)methanesulfonamideYield 45.6%

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) (250 mg, 0.451 mmol) was coupled with N-(2-morpholino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methane sulfonamide (intermediate 51) (259 mg, 0.677 mmol) in sodium carbonate (143.4 mg, 1.353 mmol), Toluene/ethanol/water (3/8/1 ml). This afforded 150 mg (45.59% yield) of the titled compound. MS: m/z=728.9 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-67d007dd3d954a45bc78818115af72c6
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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