Sodium Carbonate → HCID 57864397, compound

HRID 1672613Notes

Reaction equation

HRID 1672613 reaction equation
Br[C:2]1[CH:39]=[CH:38][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][CH2:15][N:16]([CH2:27][C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=2)[CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.[F:40][C:41]([F:52])([F:51])[C:42]1[CH:47]=[CH:46][C:45](B(O)O)=[CH:44][CH:43]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([CH2:18][CH2:17][N:16]([CH2:27][C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=2)[CH2:15][CH2:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH2:6][C:5]2[CH:38]=[CH:39][C:2]([C:45]3[CH:46]=[CH:47][C:42]([C:41]([F:52])([F:51])[F:40])=[CH:43][CH:44]=3)=[CH:3][CH:4]=2)=[CH:20][CH:21]=1)#[N:26]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 57864336Methyl 4-({{2-[2-(4-bromobenzyloxy)phenyl]ethyl}-[2-(4-cyanophenyl)ethyl]amino}methyl)benzoate

Product 1

HCID 57864397HCID 57864397, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

200 mg (0.34 mmol) of methyl 4-({{2-[2-(4-bromobenzyloxy)phenyl]ethyl}-[2-(4-cyanophenyl)ethyl]amino}methyl)benzoate from Example 9A are dissolved in 2 ml of 1,2-dimethoxyethane and, under argon, 78 mg (0.41 mmol) of 4-trifluoromethylphenylboronic acid, 2.5 mg of bis(triphenylphosphine)palladium(II) chloride and 0.38 ml of a 2 M aqueous sodium carbonate solution are added. The reaction mixture is then stirred under reflux for 12 hours. The mixture is subsequently cooled, filtered through 1 g of Extrelut, washed with dichloromethane and concentrated. The resulting crude product is purified by preparative HPLC. 158 mg (0.24 mmol, 71% yield) of a colorless oil are obtained.

Workup

  1. temperatureunder reflux for 12 hours
  2. temperatureThe mixture is subsequently cooled
  3. filtrationfiltered through 1 g of Extrelut
  4. washwashed with dichloromethane
  5. concentrationconcentrated
  6. customThe resulting crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-96a9af872c034c258d74cba56b91994e
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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