Sodium Carbonate → HCID 90030526, compound

HRID 531704Notes

Reaction equation

HRID 531704 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]([F:23])[CH:18]=4)[CH:15]=3)=[CH:9][N:8]([S:24]([C:27]3[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:5]2=[N:6][CH:7]=1.[CH3:34][C:35]1[CH:40]=[C:39](B2OC(C)(C)C(C)(C)O2)[CH:38]=[CH:37][C:36]=1[N:50]1[CH2:55][CH2:54][N:53]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:52][CH2:51]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[F:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][N:14]1[CH:15]=[C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([C:39]4[CH:38]=[CH:37][C:36]([N:50]5[CH2:51][CH2:52][N:53]([C:56]([O:58][C:59]([CH3:61])([CH3:60])[CH3:62])=[O:57])[CH2:54][CH2:55]5)=[C:35]([CH3:34])[CH:40]=4)[CH:3]=3)[N:8]([S:24]([C:27]3[CH:28]=[CH:29][C:30]([CH3:31])=[CH:32][CH:33]=3)(=[O:25])=[O:26])[CH:9]=2)[CH:12]=[N:13]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 89494140HCID 89494140, compound2×HCID 1182009745-bromo-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 90030526HCID 90030526, compoundYield 77.4%

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, 5-bromo-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (compound of Step-i of example 9) (200 g, 0.380 mmol) was coupled with tert-butyl 4-(2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine-1-carboxylate (intermediate 69A) (280 mg, 0.694 mmol) using sodium carbonate (121 mg, 1.142 mmol) and Pd(PPh3)2Cl2 (14 mg, 0.019 mmol) in DME/water (15/4 mL). This afforded 212 mg (77.3% yield) of the titled compound after purification by column (Silica gel 60/120) using 15% ethyl acetate in hexane as eluent. MS: m/z=721.3 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-e7d0e80df2f2422f90cc84e8992fb226
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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