1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 58188111, compound

HRID 1845135Notes

Reaction equation

HRID 1845135 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([CH2:10]O)=[CH:6][C:5]=12.C1C=CC(OP(OC2C=CC=CC=2)([N:21]=[N+:22]=[N-:23])=O)=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.C(Cl)Cl.O>[N:21]([CH2:10][C:7]1[CH:8]=[CH:9][N:4]2[CH:3]=[CH:2][N:1]=[C:5]2[CH:6]=1)=[N+:22]=[N-:23]

Participants

7

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 11051824Imidazo[1,2-a]pyridine-7-methanol

Product 1

HCID 58188111HCID 58188111, compoundYield 95.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of imidazo[1,2-a]pyridin-7-ylmethanol (80% purity, 1.68 g, 9.07 mmol) in toluene (40 mL) and CH2Cl2 (40 mL) at 0° C. was added diphenylphosphonic azide (3.5 mL, 16 mmol) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (2.5 mL, 17 mmol). The mixture was stirred at 0° C. for 2 h and then at rt for 16 h. The reaction mixture was diluted with water (200 mL) and CH2Cl2 (200 mL). The organic layer was separated and washed with brine, dried (Mg2SO4), filtered, and concentrated. The residue was purified by silica gel column to afford the title compound as a colorless oil (1.5 g, 75% yield for two steps).

Workup

  1. waitat rt for 16 h
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (Mg2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-4b39798112f74858ae025ec86eb34dd0
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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