Sodium Carbonate → HCID 22319565, compound

HRID 497634Notes

Reaction equation

HRID 497634 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:19]1[CH:27]=[C:26]2[C:22]([C:23]([NH:36][C:37](=[O:41])[CH2:38][CH2:39][CH3:40])=[N:24][N:25]2[CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])=[CH:21][CH:20]=1>O.O1CCOCC1.C(OCC)(=O)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>[Cl:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:27]=[C:26]3[C:22]([C:23]([NH:36][C:37](=[O:41])[CH2:38][CH2:39][CH3:40])=[N:24][N:25]3[CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:33])[CH3:34])=[CH:21][CH:20]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27343313,5-Dichlorophenylboronic acidHCID 22319559N-[6-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide

Product 1

HCID 22319565HCID 22319565, compoundYield 81.6%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

0.44 g of 3,5-dichlorophenylboronic acid, 0.64 g of sodium carbonate dissolved in 18 cm3 of water and 0.186 g of tetrakis(triphenylphosphine)palladium are added to 1 g of N-[6-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide, described previously, in 30 cm3 of dioxane, and the mixture is refluxed for 18 hours. The reaction medium is diluted with 75 cm3 of ethyl acetate and 50 cm3 of water and the medium is then filtered through a sinter funnel packed with Celite and is concentrated to dryness under reduced pressure (2 kPa; 50° C.). The work-up and the purification are performed by analogy with Example 41. 0.90 g of N-[6-(3,5-dichlorophenyl)-1-[(2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide is thus obtained in the form of a yellow wax.

Workup

  1. temperaturethe mixture is refluxed for 18 hours
  2. filtrationthe medium is then filtered through a sinter funnel
  3. concentrationis concentrated to dryness under reduced pressure (2 kPa; 50° C.)
  4. customThe work-up and the purification

Sources & evidence

ORD record
ord-b90731a1379346648025b83b2a0027ae
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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