Sodium Carbonate → N-cyclopropyl-3-fluoro-4-methyl-5-[3-(methylsulfonyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-indazol-6-yl]benzamide

HRID 1988909Notes

Reaction equation

HRID 1988909 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([S:19]([CH3:22])(=[O:21])=[O:20])=[N:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1.[CH:23]1([NH:26][C:27](=[O:45])[C:28]2[CH:33]=[C:32](B3OC(C)(C)C(C)(C)O3)[C:31]([CH3:43])=[C:30]([F:44])[CH:29]=2)[CH2:25][CH2:24]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:23]1([NH:26][C:27](=[O:45])[C:28]2[CH:33]=[C:32]([C:2]3[CH:10]=[C:9]4[C:5]([C:6]([S:19]([CH3:22])(=[O:21])=[O:20])=[N:7][N:8]4[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=3)[C:31]([CH3:43])=[C:30]([F:44])[CH:29]=2)[CH2:24][CH2:25]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 21914563N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide2×HCID 586564536-Bromo-3-(methylsulfonyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-indazole2×

Product 1

HCID 58656469N-cyclopropyl-3-fluoro-4-methyl-5-[3-(methylsulfonyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-indazol-6-yl]benzamideYield 66.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 6-bromo-3-(methylsulfonyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-indazole (Intermediate 76) (0.18 g) N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Intermediate 62) (0.14 g) aqueous sodium carbonate (1M, 1.32 ml) and tetrakis(triphenylphosphine)palladium(0) (0.01 g) in isopropanol (2 ml) was stirred at reflux under nitrogen for 18 h. The mixture was concentrated under vacuum and the residue was purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (2:1) to give the title compound (0.15 g).

Workup

  1. temperatureat reflux under nitrogen for 18 h
  2. concentrationThe mixture was concentrated under vacuum
  3. customthe residue was purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-972ccb00eb674d65942fda9bede9db2a
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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