Sodium Carbonate → HCID 118524039, compound

HRID 531566Notes

Reaction equation

HRID 531566 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]3[N:10]([S:14]([C:17]4[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=4)(=[O:16])=[O:15])[CH:11]=[C:12](I)[C:7]3=[CH:6][C:5]=2[C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]3)=[CH:26][CH:25]=2)[CH2:3][CH2:2]1.[F:43][C:44]1[CH:45]=[C:46]([CH:64]=[CH:65][CH:66]=1)[CH2:47][N:48]1[C:52]([CH3:53])=[C:51](B2OC(C)(C)C(C)(C)O2)[C:50]([CH3:63])=[N:49]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.COCCOC.O>[CH:1]1([C:4]2[N:9]=[C:8]3[N:10]([S:14]([C:17]4[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=4)(=[O:16])=[O:15])[CH:11]=[C:12]([C:51]4[C:50]([CH3:63])=[N:49][N:48]([CH2:47][C:46]5[CH:64]=[CH:65][CH:66]=[C:44]([F:43])[CH:45]=5)[C:52]=4[CH3:53])[C:7]3=[CH:6][C:5]=2[C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]3)=[CH:26][CH:25]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 900306711-(3-Fluoro-benzyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole2×HCID 90030880HCID 90030880, compound2×

Product 1

HCID 118524039HCID 118524039, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-1, tert-butyl 4-(4-(6-cyclopropyl-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (intermediate 47) (115 mg, 0.161 mmol) was coupled with 1-(3-fluorobenzyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 16) (81.53 mg, 0.24 mmol) in sodium carbonate (51.9 mg, 0.483 mmol), Pd(PPh3)2Cl2 (5.6 mg, 0.008 mmol), 1,2-dimethoxyethane/water (10/2 ml) to afford 113 mg (89% yield) of titled compound.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-5eaaf6678e774bffa4b74d45b181caec
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…