Sodium Carbonate → HCID 18694229, compound

HRID 1870891Notes

Reaction equation

HRID 1870891 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5](Br)=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.B([C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1)(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.[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>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 678524-Bromo-3-(trifluoromethyl)anilineHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 18694229HCID 18694229, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred solution of 5-amino-2-bromobenzotrifluoride (2.5 g, 0.01 mol) in DME (60 ml) and water (60 ml) was treated with 4-boronobenzoic acid (1.65 g, 0.01 mol) and Na2CO3 (4.2 g, 0.04 mol). The mixture was degassed with argon for 15 mins, treated with tetrakis (triphenylphosphine) palladium (O) (230 mg, 0.2 mmol) and heated at reflux under argon for 18 hrs. The mixture was concentrated in vacuo to approx. 50% volume and the aqueous residue treated with 10% aqueous Na2CO3 solution and washed with ethyl acetate. The aqueous layer was separated, acidified with 5M HCl and concentrated in vacuo to afford an off-white solid containing the title compound. This was used in the next step without further purification.

Workup

  1. customThe mixture was degassed with argon for 15 mins
  2. temperatureheated
  3. temperatureat reflux under argon for 18 hrs
  4. concentrationThe mixture was concentrated in vacuo to approx. 50% volume
  5. additionthe aqueous residue treated with 10% aqueous Na2CO3 solution
  6. washwashed with ethyl acetate
  7. customThe aqueous layer was separated
  8. concentrationconcentrated in vacuo
  9. customto afford an off-white solid

Sources & evidence

ORD record
ord-4e7cdeb389ed42509d62f0f3e6fe91d7
Source dataset
uspto-grants-2000_08
Patent number
US06100272

Reaction notes

Loading…