1,2-Dimethoxyethane → HCID 135961516, compound

HRID 2353053Notes

Reaction equation

HRID 2353053 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][OH:14])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[OH:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.COCCOC.[OH-].[Na+]>O.[Na+].[Cl-].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>[OH:14][CH2:13][CH2:12][NH:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:19]3[CH:20]=[CH:21][C:16]([OH:15])=[CH:17][CH:18]=3)=[CH:3][N:4]=2)[N:7]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 14798Sodium Hydroxide2×HCID 27343604-Hydroxyphenylboronic acidHCID 57418689HCID 57418689, compound

Product 1

HCID 135961516HCID 135961516, compoundYield 44.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 5234Sodium ChlorideSolvent

Conditions

Temperature
90 °C

Procedure

85 mg (0.33 mmol) of 2-(3-bromoimidazo[1,2-b]pyridazin-6-ylamino)ethanol (Example 1.5), 69 mg (0.5 mmol) of 4-hydroxybenzene boronic acid and 76 mg (0.066 mmol) of tetrakis(triphenylphosphine)palladium(0) were mixed under argon with 3.4 ml of dimethyl glycol and 2 ml of an aqueous NaOH solution (a stock solution of 190 mg of NaOH in 10 ml of water). The mixture was stirred at 90° C. for 19 hours. After cooling, the mixture was diluted with sat. NaCl solution and extracted 2× with ethyl acetate. The combined organic phases were washed with sat. NaCl solution, filtered through a silicone filter (from Whatman) and concentrated. The resulting crude product was recrystallized from methanol. 40 mg of the desired product are obtained.

Workup

  1. temperatureAfter cooling
  2. extractionextracted 2× with ethyl acetate
  3. washThe combined organic phases were washed with sat. NaCl solution
  4. filtrationfiltered through a silicone
  5. filtrationfilter (from Whatman)
  6. concentrationconcentrated
  7. customThe resulting crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-0c182f58604f42139f139eaf7e9414aa
Source dataset
uspto-grants-2010_07
Patent number
US07750000B2

Reaction notes

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