Cesium carbonate → HCID 70982207, compound

HRID 1409441Notes

Reaction equation

HRID 1409441 reaction equation
Br[C:2]1[N:3]([CH3:17])[CH:4]=[C:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[N:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:24]1(B(O)O)[CH2:26][CH2:25]1>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>[CH:24]1([C:2]2[N:3]([CH3:17])[CH:4]=[C:5]([C:7]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:8])[N:6]=2)[CH2:26][CH2:25]1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 2760897Cyclopropylboronic acidHCID 70980972HCID 70980972, compound

Product 1

HCID 70982207HCID 70982207, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

Into a solution of benzyl 2-bromo-1-methyl-1H-imidazole-4-carboxylate (2.8 g, 9.49 mmol) in THF (40 ml) and water (20 ml), cesium carbonate (7.71 g, 23.7 mmol) and cyclopropyl boronic acid (1.22 g, 14.2 mmol) were added under argon atmosphere at RT. The resulting mixture was degassed and purged with argon for 10 min. Pd(PPh3)2Cl2 (0.332 g, 0.04 mmol) was added to the mixture and heated at 100° C. for 12 h. The reaction mixture was filtered through a celite bed and the filtrate was diluted with water and extracted with EtOAc. The organic layer was concentrated and purified by flash chromatography. Yield 1.1 g. 1H-NMR (400 MHz; CDCl3): δ 0.95-1.02 (m, 2H), 1.07-1.11 (m, 2H), 1.72-1.78 (m, 1H), 3.70 (s, 3H), 5.32 (s, 2H), 7.29 (s, 1H), 7.42-7.62 (m, 5H), LC-MS: [M+1]=257.

Workup

  1. customThe resulting mixture was degassed
  2. custompurged with argon for 10 min
  3. filtrationThe reaction mixture was filtered through a celite bed
  4. additionthe filtrate was diluted with water
  5. extractionextracted with EtOAc
  6. concentrationThe organic layer was concentrated
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-e3bdc12f68d443bca34ec2d6467f236f
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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