Sodium Carbonate → tert-butyl 5-(3-(methylsulfonamido)phenyl)-3-(1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

HRID 531480Notes

Reaction equation

HRID 531480 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:12]=3)[CH:9]=2)[N:4]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:3]=1.[N+:29]([C:32]1[CH:33]=[C:34]([CH:50]=[CH:51][CH:52]=1)[CH2:35][N:36]1[CH:40]=[C:39](B2OC(C)(C)C(C)(C)O2)[CH:38]=[N:37]1)([O-:31])=[O:30].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].COCCOC.O>[CH3:21][S:18]([NH:17][C:13]1[CH:12]=[C:11]([C:8]2[CH:9]=[C:10]3[C:2]([C:39]4[CH:38]=[N:37][N:36]([CH2:35][C:34]5[CH:50]=[CH:51][CH:52]=[C:32]([N+:29]([O-:31])=[O:30])[CH:33]=5)[CH:40]=4)=[CH:3][N:4]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:5]3=[N:6][CH:7]=2)[CH:16]=[CH:15][CH:14]=1)(=[O:20])=[O:19]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 900309041H-Pyrazole, 1-[(3-nitrophenyl)methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2×HCID 90031437tert-butyl 3-iodo-5-(3-(methylsulfonamido)phenyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 118523971tert-butyl 5-(3-(methylsulfonamido)phenyl)-3-(1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylateYield 68%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

Using similar reaction conditions as described in step-i of example 1, tert-butyl 3-iodo-5-(3-(methylsulfonamido)phenyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (intermediate-32) (300 mg, 0.5 mmol) was coupled with 1-(3-nitrobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 10) (211 mg, 0.6 mmol) in sodium carbonate (189 mg, 1.7 mmol), PdCl2(dppf) (20 mg, 0.02 mmol) and DME/water (3/3 ml) to afford 200 mg (59% yield) of the pure product after column purification using 30% ethyl acetate in hexane as eluent.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-c6c56c1d34504ac68dbf6489ef694ff2
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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