Sodium Carbonate → HCID 59223188, compound

HRID 473264Notes

Reaction equation

HRID 473264 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[N:9]([C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]([CH:34]3[CH2:36][CH2:35]3)=[CH:26][CH:25]=2)[C:10]([S:13][C:14]([CH3:23])([CH3:22])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[N:11][N:12]=1.[C:37]1(B(O)O)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1(C)C=CC=CC=1.C1COCC1.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>[CH:34]1([C:27]2[C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:24]([N:9]3[C:8]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[N:12][N:11]=[C:10]3[S:13][C:14]([CH3:23])([CH3:22])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:25][CH:26]=2)[CH2:36][CH2:35]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 46178845HCID 46178845, compound

Product 1

HCID 59223188HCID 59223188, compoundYield 73.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

Aqueous sodium carbonate solution (1M, 614 μL, 0.614 mmol) was added to a solution of tert-butyl 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)-2-methylpropanoate (60 mg, 0.123 mmol), phenylboronic acid (17 mg, 0.135 mmol) and Pd(PPh3)4 (28 mg, 0.024 mmol) in toluene (2 mL) and THF (1 mL). The mixture was bubbled under nitrogen for 5 mins and then heated to 90° C. under nitrogen for 20 hours. After cooling to room temp, water (20 mL) was added and the aqueous layer extracted with dichloromethane (2×20 mL). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered, concentrated and purified by column chromatography (40% EtOAc/hexanes) to give tert-butyl 2-(4-(4-cyclopropylnaphthalen-1-yl)-5-phenyl-4H-1,2,4-triazol-3-ylthio)-2-methylpropanoate as a brown oil (44 mg, 73%).

Workup

  1. customThe mixture was bubbled under nitrogen for 5 mins
  2. temperatureAfter cooling to room temp
  3. additionwater (20 mL) was added
  4. extractionthe aqueous layer extracted with dichloromethane (2×20 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by column chromatography (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a07f77a9bae0457f976a1e67455f6aec
Source dataset
uspto-grants-2014_01
Patent number
US08633232B2

Reaction notes

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