Sodium Carbonate → HCID 69084916, compound

HRID 594394Notes

Reaction equation

HRID 594394 reaction equation
P(OC1C=CC=CC=1)(OC1C=CC=CC=1)(O[C:4]1[N:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=2)[C:6](=[O:10])[CH2:7][CH2:8][CH:9]=1)=O.[CH2:37]([O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1B(O)O)[CH3:38].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O.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>[CH2:37]([O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:4]1[N:5]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:16][CH:17]=2)[C:6](=[O:10])[CH2:7][CH2:8][CH:9]=1)[CH3:38]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734902(2-Ethoxyphenyl)boronic acidHCID 69083750HCID 69083750, compound

Product 1

HCID 69084916HCID 69084916, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 6-oxo-1-(4-(trifluoromethoxy)benzyl)-1,4,5,6-tetrahydropyridin-2-yl diphenyl phosphate (140 mg; 0.13 mmol; 1.0 equiv.), (2-ethoxyphenyl)boronic acid (34 mg; 0.20 mmol; 1.5 equiv.), PdCl2(PPh3)2 (5 mg; 0.007 mmol; 0.05 equiv.), Na2CO3 (188 mg; 1.78 mmol; 13.2 equiv.) in THF (2 ml) and water (0.9 ml) was heated to 40° C., under nitrogen, for 1.5 h. After cooling to rt, water was added, and the mixture was extracted with Et2O (3×). The mixed organic layers were dried over anh. K2CO3, filtered, and concentrated to dryness under reduced pressure. Purification by preparative HPLC afforded 6-(2-ethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)-3,4-dihydropyridin-2(1H)-one. LC-MS (conditions E): tR=0.83 min.; [M+H]+: 392.2 g/mol.

Workup

  1. temperatureAfter cooling to rt
  2. extractionthe mixture was extracted with Et2O (3×)
  3. dry with materialThe mixed organic layers were dried over anh. K2CO3
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-a7bf144f7a5a4bb8ace0e8e5f2ea20cb
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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