1,3-Propanediol → HCID 16128671, compound

HRID 2266413Notes

Reaction equation

HRID 2266413 reaction equation
Br[C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:8]=[C:9]([NH:13][C:14](=[O:16])[CH3:15])[CH:10]=[CH:11][CH:12]=2)[CH:6]=1.[CH3:17][C:18]1[O:22][C:21](B(O)O)=[CH:20][CH:19]=1.C([O-])([O-])=O.[Cs+].[Cs+].C(O)CCO>CC#N>[CH3:17][C:18]1[O:22][C:21]([C:2]2[N:3]=[CH:4][N:5]([C:7]3[CH:8]=[C:9]([NH:13][C:14](=[O:16])[CH3:15])[CH:10]=[CH:11][CH:12]=3)[CH:6]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 104421,3-PropanediolHCID 10796Cesium carbonateHCID 27343725-Methyl-2-furanboronic AcidHCID 59599656HCID 59599656, compound

Product 1

HCID 16128671HCID 16128671, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
170 °C

Procedure

A slurry of 12 (140 mg; 0.5 mmol), 5-methylfuran-2-boronic acid (88.1 mg; 0.7 mmol), Cs2CO3 (179 mg, 0.55 mmol) and propane-1,3-diol (53 mg; 1.4 mmol) in CH3CN (4 mL) was purged with argon and Cl2Pd(PPh3)2 (7 mg; 2 mol %) was added. The mixture was heated in EmrysOptimiser (170° C., 15 min). The reaction mixture was filtered hot through a fritte and the precipitate was extracted with hot CH3CN (8 mL), which was filtered through the same fritte and pooled with the first fraction. The yellow solution was evaporated to dryness and redissolved in 1 mL CH3CN which was purified by preparative LC-MS to give pure title compound 16 mg (11%). HRMS (ESI+): m/z=281.3135 [M+H]

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered hot through a fritte
  3. extractionthe precipitate was extracted with hot CH3CN (8 mL), which
  4. filtrationwas filtered through the same fritte
  5. customThe yellow solution was evaporated to dryness
  6. dissolutionredissolved in 1 mL CH3CN which
  7. customwas purified by preparative LC-MS

Sources & evidence

ORD record
ord-6a4acd36d2954a0fb1ec28020c25a3e7
Source dataset
uspto-grants-2010_12
Patent number
US07858649B2

Reaction notes

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