Sodium Carbonate → HCID 58924894, compound

HRID 1990997Notes

Reaction equation

HRID 1990997 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1B(O)O)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].Br[C:20]1[S:21][CH:22]=[C:23]([C:25]([N:27]2[CH:36]3[CH:31]([CH2:32][CH2:33][CH2:34][CH2:35]3)[CH2:30][CH2:29][CH2:28]2)=[O:26])[N:24]=1>COCCOC.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>[N:27]1([C:25]([C:23]2[N:24]=[C:20]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:1](=[O:3])[CH3:2])[S:21][CH:22]=2)=[O:26])[CH:36]2[CH:31]([CH2:32][CH2:33][CH2:34][CH2:35]2)[CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343092-Acetylphenylboronic acidHCID 58924815HCID 58924815, compound

Product 1

HCID 58924894HCID 58924894, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

In a Microwave process tube, tetrakis(triphenylphosphine)palladium (5 mg, 0.004 mmol) was added to a degassed (nitrogen) mixture of 2-acetylphenylboronic acid (Aldrich; 38 mg, 0.15 mmol) and sodium carbonate (2 M in water, 0.2 mL, 0.4 mmol), and (2-bromo-thiazol-4-yl)-(octahydro-qunolin-1-yl)-methanone (from Step 1; 50 mg, 0.15 mmol) in DME (dry, 1.5 mL). The tube was submitted to 150 W Microwave Irradiation at 160° C. for 5 minutes. The reaction mixture was cooled to room temperature, filtered through celite and silica plug, and extracted with EtOAc and water three times. The organic layers were combined, concentrated and purified by C-18 reversed phase HPLC with a gradient of 10-100% Acetonitrile/Water to give 1-{2-[4-(octahydro-quinoline-1-carbonyl)-thiazol-2-yl]-phenyl}-ethanone (40 mg, 70%).

Workup

  1. customa degassed
  2. customThe tube was submitted to 150 W Microwave Irradiation at 160° C. for 5 minutes
  3. filtrationfiltered through celite and silica plug
  4. extractionextracted with EtOAc and water three times
  5. concentrationconcentrated
  6. custompurified by C-18

Sources & evidence

ORD record
ord-c866adef174242d0bd8470532d78fea6
Source dataset
uspto-grants-2010_01
Patent number
US07645773B2

Reaction notes

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