Benzyl Bromide → HCID 59753827, compound

HRID 1453685Notes

Reaction equation

HRID 1453685 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][C:22]([OH:24])=[O:23])[CH:13]=2)=[N:4][NH:3]1.C([O-])([O-])=O.[K+].[K+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C>[CH2:31]([N:3]1[C:2](=[O:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][C:22]([OH:24])=[O:23])[CH:13]=2)=[N:4]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7498Benzyl Bromide2×HCID 11430Potassium Carbonate2×HCID 67316971HCID 67316971, compound

Product 1

HCID 59753827HCID 59753827, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

The product of step c) was dissolved in DMF (4 mL) and treated with K2CO3 (55 mg, 0.4 mmol) and benzyl bromide (0.25 mmol). The reaction was heated to 70° C. for 12 h. Additional K2CO3 (0.2 mmol) and benzyl bromide (0.25 mmol) was added and heating was continued for 3 h. The reaction was cooled and partitioned between EtOAc and water. The organic layer was washed 3 times with water and concentrated. The residue was dissolved in EtOH (2 mL) and treated with NaOH (0.5 mL, 1 M). After heating to 70° C. for 1 h, the reaction was cooled, acidified with HCl, and extracted into DCM. The organic layer was concentrated, dissolved in DMF, and purified by preparative LCMS. 1H NMR (DMSO-d6) δ 8.41 (d, J=6.9 Hz, 1H), 8.16 (d, J=7.2 Hz, 1H), 7.98-7.89 (m, 2H), 7.87 (s, 1H), 7.61 (d, J=8.1 Hz, 1H), 7.44-7.27 (m, 6H), 7.17 (t, J=7.3 Hz, 1H), 7.03 (t, J=7.5 Hz, 1H), 5.43 (s, 2H), 4.80 (s, 2H); MS: ESI (negative): 408 (M−H).

Workup

  1. temperatureheating
  2. temperatureThe reaction was cooled
  3. custompartitioned between EtOAc and water
  4. washThe organic layer was washed 3 times with water
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in EtOH (2 mL)
  7. additiontreated with NaOH (0.5 mL, 1 M)
  8. temperatureAfter heating to 70° C. for 1 h
  9. temperaturethe reaction was cooled
  10. extractionextracted into DCM
  11. concentrationThe organic layer was concentrated
  12. dissolutiondissolved in DMF
  13. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-acef67be7a03478a87fe2efd3a2be23b
Source dataset
uspto-grants-2009_01
Patent number
US07476667B2

Reaction notes

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