Sodium Iodide → HCID 22031173, compound

HRID 1792448Notes

Reaction equation

HRID 1792448 reaction equation
[Br:1][C:2]1[C:3]([C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)=[N:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.Br[CH2:34][CH2:35][O:36][CH2:37][CH2:38]Br.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C.CN(C)C=O>[Br:1][C:2]1[C:3]([C:26]2[CH:31]=[CH:30][C:29]([N:32]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[CH:28][CH:27]=2)=[N:4][N:5]([C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 22032174HCID 22032174, compound

Product 1

HCID 22031173HCID 22031173, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2.4 g 4-(4-bromo-1-trityl-1H-pyrazol-3-yl)phenylamine (compound in Production Example 152), 0.7 mL 2-bromoethyl ether, 80 mg sodium iodide, 1.52 g potassium carbonate and 50 mL N,N-dimethylformamide was stirred at 80° C. for 3 days. Ethyl acetate and water were added to the reaction solution, then water was added thereto, and the organic layer was separated, washed with an aqueous saturated solution of sodium bicarbonate, water and brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was evaporated. The resulting residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 1.21 g of the title compound as a pale yellow amorphous.

Workup

  1. customthe organic layer was separated
  2. washwashed with an aqueous saturated solution of sodium bicarbonate, water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe filtrate was evaporated
  6. customThe resulting residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9de829fad7074c198d36aaffabd3acbe
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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