Sodium Carbonate → N-(3-(1-tosyl-3-(1-(3-(trifluoromethyl)benzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide

HRID 531468Notes

Reaction equation

HRID 531468 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]([C:23]([F:26])([F:25])[F:24])[CH:18]=4)[CH:15]=3)=[CH:9][N:8]([S:27]([C:30]3[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[C:5]2=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:45]2[CH:46]=[C:47]([NH:51][S:52]([CH3:55])(=[O:54])=[O:53])[CH:48]=[CH:49][CH:50]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>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>[S:27]([N:8]1[C:5]2=[N:6][CH:7]=[C:2]([C:45]3[CH:46]=[C:47]([NH:51][S:52]([CH3:55])(=[O:53])=[O:54])[CH:48]=[CH:49][CH:50]=3)[CH:3]=[C:4]2[C:10]([C:11]2[CH:12]=[N:13][N:14]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)[CH:15]=2)=[CH:9]1)([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 162177153-(Methanesulfonylamino)phenylboronic acid pinacol ester2×HCID 900305735-bromo-1-tosyl-3-(1-(3-(trifluoromethyl)benzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 90031373N-(3-(1-tosyl-3-(1-(3-(trifluoromethyl)benzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamideYield 100.9%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

Using similar reaction conditions as described in step 2 of example 1, 5-bromo-1-tosyl-3-(1-(3-(trifluoromethyl)benzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine (165 mg, 0.28 mmol) was coupled with N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl) methane sulfonamide (Intermediate 3) (119 mg, 0.401 mmol) in sodium carbonate (91 mg, 0.86 mmol), bis(triphenyl phosphine)palladium(ii) dichloride (10 mg, 0.014 mmol) and toluene/ethanol/water (15/6/2 ml) to afford 188 mg (98.4% yield) of the pure product after column purification using 60% ethyl acetate in hexane as eluent. MS: m/z=666.10 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-a48634a48b25450f880d43f461b0b5a2
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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