N-(2-Morpholino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)methanesulfonamide → N-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-morpholinophenyl) methanesulfonamide

HRID 531498Notes

Reaction equation

HRID 531498 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=4)[CH:15]=3)=[CH:9][N:8]([S:24]([C:27]3[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:5]2=[N:6][CH:7]=1.[O:34]1[CH2:39][CH2:38][N:37]([C:40]2[CH:45]=[CH:44][C:43](B3OC(C)(C)C(C)(C)O3)=[CH:42][C:41]=2[NH:55][S:56]([CH3:59])(=[O:58])=[O:57])[CH2:36][CH2:35]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1.C(O)C.O>[F:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][N:14]1[CH:15]=[C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([C:43]4[CH:44]=[CH:45][C:40]([N:37]5[CH2:36][CH2:35][O:34][CH2:39][CH2:38]5)=[C:41]([NH:55][S:56]([CH3:59])(=[O:57])=[O:58])[CH:42]=4)[CH:3]=3)[N:8]([S:24]([C:27]3[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=3)(=[O:25])=[O:26])[CH:9]=2)[CH:12]=[N:13]1

Participants

5

Reactant 2

HCID 90064794N-(2-Morpholino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)methanesulfonamide2×HCID 1182009745-bromo-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 118523922N-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-morpholinophenyl) methanesulfonamideYield 90.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-1, 5-bromo-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine Compound of step-I in Example 9) (200 mg, 0.3809 mmol) was coupled with N-(2-morpholino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methane sulfonamide (Intermediate 20) (220 mg, 0.5714 mmol), Pd(PPh3)2Cl2 (13.5 mg, 0.01904 mmol), Toluene/ethanol/water (20/10/4 ml) to afford 240 mg (90.2% yield) of the titled compound.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-04ecba45bf89471aa87b4096cccef7e4
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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