(4-Aminophenoxy)benzene → HCID 21025113, compound

HRID 1796596Notes

Reaction equation

HRID 1796596 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:18])=[C:8]2[C:13](Cl)=[C:12]([C:15]#[N:16])[CH:11]=[N:10][N:9]2[CH:17]=1)=[O:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].[O:25]([C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C.ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:18])=[C:8]2[C:13]([NH:36][C:35]3[CH:34]=[CH:33][C:32]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:38][CH:37]=3)=[C:12]([C:15]#[N:16])[CH:11]=[N:10][N:9]2[CH:17]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 8764(4-Aminophenoxy)benzeneHCID 11430Potassium CarbonateHCID 21025099HCID 21025099, compound

Product 1

HCID 21025113HCID 21025113, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 1D (26 mg, 0.10 mmol) in DMF (2 mL) were added K2CO3 (138 mg, 1.00 mmol) and p-phenoxyaniline (20 mg, 0.11 mmol) at 25° C. The reaction mixture was stirred for 12 h and then diluted with dichloromethane (15 mL) and washed with water (10 mL) and brine (10 mL). The organic phase was dried over Na2SO4 and concentrated and the resulting residue was triturated with methanol to afford 31 mg (76% yield) of the desired compound as a yellow solid. HPLC: 100% at 4.62 min (retention time) (YMC S5 ODS column, 4.6×50 mm, eluting with 10-90% aqueous methanol over 4 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 413.12 [M+H]+.

Workup

  1. washwashed with water (10 mL) and brine (10 mL)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customthe resulting residue was triturated with methanol

Sources & evidence

ORD record
ord-6e264df2306845b7a5cdf27995abbd15
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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