1,2-Dimethoxyethane → [4-(3-Bromo-4-methoxy-benzyl)-phenyl]-urea

HRID 1632039Notes

Reaction equation

HRID 1632039 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8]Br)[CH:5]=[CH:4][C:3]=1[O:10][CH3:11].CC1(C)C(C)(C)OB([C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH2:29])=[O:28])=[CH:22][CH:21]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(COC)OC>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[O:10][CH3:11])[CH2:8][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH2:29])=[O:28])=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 112774622-Bromo-4-(bromomethyl)-1-methoxybenzeneHCID 167274404-(Carbamoylamino)benzeneboronic acid, pinacol ester

Product 1

HCID 57703725[4-(3-Bromo-4-methoxy-benzyl)-phenyl]-ureaYield 36.9%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a 40 mL vial equipped with a teflon screw cap and a magnetic stir bar was added 2-bromo-4-bromomethyl-1-methoxybenzene (649 mg, 2.32 mmol), [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-urea (577 mg, 2.20 mmol) and potassium phosphate (933 mg, 4.40 mmol). To the vial was then added dimethoxyethane (15 mL), ethanol (3.7 mL) and water (3.7 mL). To this stirring solution was added tetrakis(triphenylphosphine) palladium (127 mg, 0.11 mmol) and the solution was degassed by bubbling N2 gas through the solution for 20 min. The vial was capped and placed in an oil bath with stirring at 65° C. for 12.5 h. The cooled reaction mixture was concentrated under a stream of N2 gas to a total volume of ˜5 mL and then diluted with ethyl acetate (20 mL) and water (10 mL). Upon shaking a white solid precipitates. The solid is filtered and dried to afford 272 mg (34%) of [4-(3-bromo-4-methoxy-benzyl)-phenyl]-urea (I-44) as a white solid.

Workup

  1. customscrew cap
  2. customthe solution was degassed
  3. customby bubbling N2 gas through the solution for 20 min
  4. customThe vial was capped
  5. customplaced in an oil bath
  6. customThe cooled reaction mixture
  7. concentrationwas concentrated under a stream of N2 gas to a total volume of ˜5 mL
  8. additiondiluted with ethyl acetate (20 mL) and water (10 mL)
  9. stirringUpon shaking a white solid
  10. customprecipitates
  11. filtrationThe solid is filtered
  12. customdried

Sources & evidence

ORD record
ord-6f485a0cb96a40f180a0a703e3c69b5c
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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