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

HRID 531748Notes

Reaction equation

HRID 531748 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.CC1(C)C(C)(C)OB([C:48]2[CH:49]=[N:50][N:51]([CH2:53][C:54]3[CH:55]=[N:56][CH:57]=[CH:58][CH:59]=3)[CH:52]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.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>[N:56]1[CH:57]=[CH:58][CH:59]=[C:54]([CH2:53][N:51]2[CH:52]=[C:48]([C:2]3[C:10]4[C:5](=[N:6][CH:7]=[C:8]([C:11]5[CH:16]=[CH:15][C:14]([N:17]6[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]6)=[CH:13][CH:12]=5)[CH:9]=4)[N:4]([S:30]([C:33]4[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=4)(=[O:32])=[O:31])[CH:3]=3)[CH:49]=[N:50]2)[CH:55]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 179991853-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyridine2×HCID 90030611tert-butyl 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate2×

Product 1

HCID 118523965tert-butyl 4-(4-(3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylateYield 72.5%

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) (150 mg, 0.22 mmol) was coupled with 3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyridine (intermediate 64) (130 mg, 0.45 mmol) using sodium carbonate (70 mg, 0.66 mmol) and Pd(PPh3)2Cl2 (7.7 mg, 0.011 mmol) in toluene/ethanol/water (10/10/2 ml) to give 110 mg (70% yield) of the titled compound after purification by column (Silica gel 60/120) using 35% ethyl acetate in hexane as eluent.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-b5f9f427d3fa4bada1136c64afe4a30b
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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