Potassium Carbonate → HCID 59464307, compound

HRID 1713841Notes

Reaction equation

HRID 1713841 reaction equation
[CH2:1]([N:8]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:32]1[CH:33]=[C:34]([CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH:35]=[CH:36][CH:37]=1>C1(C)C=CC=CC=1.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>[CH2:1]([N:8]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:9]1[CH:14]=[CH:13][C:12]([C:36]2[CH:37]=[CH:32][CH:33]=[C:34]([CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH:35]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11470552Ethyl 3-(bromophenyl)acetateHCID 18979386[4-(Dibenzylamino)phenyl]boronic acid

Product 1

HCID 59464307HCID 59464307, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent3×

Conditions

Temperature
90 °C

Procedure

[4-(Dibenzylamino)phenyl]boronic acid (UK Patent Application No. GB 2276161 (1994)) (400 mL, 1.26 mmol) was stirred in 5 mL dry toluene and potassium carbonate was added followed by ethyl (3-bromophenyl)acetate (338 mg, 1.39 mmol) as a solution in toluene (1 mL). The reaction vessel was evacuated and refilled with nitrogen (5 times). Pd(PPh3)4 (73 mg, 0.06 mmol) was added as a solution in toluene (1 mL) and the vessel was deoxygenated as before. The reaction mixture was heated at 90° C. for 16 h then cooled and filtered through diatomaceous earth. Volatile material was removed by evaporation, the residue was adsorbed onto silica and purified by chromatography eluting with 10-50% EtOAc/isohexane to give the title compound (175 mg, 32%) as a gum; 1H NMR δ 1.18 (t, 3H), 3.67 (s, 2H), 4.07 (q, 2H), 4.76 (s, 4H), 6.76 (d, 2H), 7.11 (d, 2H), 7.44-7.20 (m, 14H); MS m/e MH+ 436.

Workup

  1. customThe reaction vessel was evacuated
  2. additionrefilled with nitrogen (5 times)
  3. customthe vessel was deoxygenated as before
  4. temperaturethen cooled
  5. filtrationfiltered through diatomaceous earth
  6. customVolatile material was removed by evaporation
  7. custompurified by chromatography
  8. washeluting with 10-50% EtOAc/isohexane

Sources & evidence

ORD record
ord-5f1db610f0f7440c9492e5a55450c93d
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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