Sodium Carbonate → tert-butyl 4-(4-(3-(1-(2,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate

HRID 531542Notes

Reaction equation

HRID 531542 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)=[CH:13][CH:12]=3)[CH:9]=2)[N:4]([S:30]([C:33]2[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[CH:3]=1.[F:40][C:41]1[CH:63]=[CH:62][C:61]([F:64])=[CH:60][C:42]=1[CH2:43][N:44]1[C:48]([CH3:49])=[C:47](B2OC(C)(C)C(C)(C)O2)[C:46]([CH3:59])=[N:45]1.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>[F:40][C:41]1[CH:63]=[CH:62][C:61]([F:64])=[CH:60][C:42]=1[CH2:43][N:44]1[C:48]([CH3:49])=[C:47]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:16]=[CH:15][C:14]([N:17]5[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]5)=[CH:13][CH:12]=4)[CH:9]=3)[N:4]([S:30]([C:33]3[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[CH:3]=2)[C:46]([CH3:59])=[N:45]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 90030611tert-butyl 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate2×HCID 900311871-[(2,5-Difluorophenyl)methyl]-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazole2×

Product 1

HCID 90033968tert-butyl 4-(4-(3-(1-(2,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylateYield 125.7%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-1, tert-butyl 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (intermediate 41) (160 mg, 0.243 mmol) was coupled with 1-(2,5-difluorobenzyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 25) (85 mg, 0.243 mmol) in sodium carbonate (77 mg, 0.729 mmol), Pd(PPh3)2Cl2 (17 mg, 0.0243 mmol), Toluene/ethanol/water (15/7.5/1 ml) to give 230 mg of titled compound. MS: m/z=753.1 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-5e44f0af532e467da6c6702d641c2c9a
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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