Potassium Carbonate → HCID 59333343, compound

HRID 1893440Notes

Reaction equation

HRID 1893440 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[CH:13][N:14]=[C:7]1[C:6]([NH:15][CH2:16][CH2:17][CH2:18][OH:19])=[N:5]2.[F:20][C:21]([F:32])([F:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>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.O.COCCOC>[F:20][C:21]([F:32])([F:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[CH:13][N:14]=[C:7]1[C:6]([NH:15][CH2:16][CH2:17][CH2:18][OH:19])=[N:5]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 25070095HCID 25070095, compound

Product 1

HCID 59333343HCID 59333343, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (11 mg, 0.009 mmol, 0.1 eq), 3-(7-Bromo-imidazo[1,2-a]quinoxalin-4-ylamino)-propan-1-ol (30 mg, 0.093 mmol, 1 eq), 2-(trifluoromethyl)phenylboronic acid (19 mg, 0.102 mmol, 1.1 eq), potassium carbonate (51 mg, 0.372 mmol, 4 eq) are stirred under argon in a mixture of degassed water/1,2-dimethoxyethane (1 mL/1 mL) at 80° C. for 3 days. Evaporation of 1,2-dimethoxyethane, partition (water/ethyl acetate), extraction of the aqueous phase (two times ethyl acetate), reunion of the organic phases, drying over magnesium sulfate and purification over silicagel on prep TLC (eluent: dichloromethane/methanol 90:10) affords the title compound as an off-white solid (14 mg, 0.036 mmol, 39%).

Workup

  1. customEvaporation of 1,2-dimethoxyethane
  2. custompartition
  3. extraction(water/ethyl acetate), extraction of the aqueous phase (two times ethyl acetate), reunion of the organic phases
  4. dry with materialdrying over magnesium sulfate and purification over silicagel on prep TLC (eluent: dichloromethane/methanol 90:10)

Sources & evidence

ORD record
ord-4d1615bc1210461ca2159c1f2502f0da
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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