Sodium Carbonate → HCID 58656465, compound

HRID 1988904Notes

Reaction equation

HRID 1988904 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)(=[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:29]1([NH:32][C:33](=[O:50])[C:34]2[CH:39]=[CH:38][C:37]([CH3:40])=[C:36](B3OC(C)(C)C(C)(C)O3)[CH:35]=2)[CH2:31][CH2:30]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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:29]1([NH:32][C:33](=[O:50])[C:34]2[CH:39]=[CH:38][C:37]([CH3:40])=[C:36]([C:2]3[CH:10]=[C:9]4[C:5]([C:6]([S:19]([C:22]5[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=5)(=[O:21])=[O:20])=[N:7][N:8]4[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:16])[CH3:17])=[CH:4][CH:3]=3)[CH:35]=2)[CH2:30][CH2:31]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide2×HCID 58656455HCID 58656455, compound2×

Product 1

HCID 58656465HCID 58656465, compoundYield 69.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 6-bromo-3-[(4-fluorophenyl)sulfonyl]-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-indazole (Intermediate 70) (0.06 g) N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Intermediate 5) (0.04 g) aqueous sodium carbonate (1M, 0.66 ml) and tetrakis(triphenylphosphine)palladium(0) (0.015 g) in 1,2-dimethoxyethane (4 ml) was stirred at reflux under nitrogen for 18 h. The mixture was concentrated under vacuum and the residue was purified on a Varian Bond-Elut SPE cartridge, eluting with cyclohexane:ethyl acetate (100:0 to 50:50) to give the title compound (0.05 g).

Workup

  1. temperatureat reflux under nitrogen for 18 h
  2. concentrationThe mixture was concentrated under vacuum
  3. customthe residue was purified on a Varian Bond-Elut SPE cartridge
  4. washeluting with cyclohexane:ethyl acetate (100:0 to 50:50)

Sources & evidence

ORD record
ord-e313249ce2ef451b8ce4a0bf09d1eeb7
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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