Benzyl Bromide → HCID 67071797, compound

HRID 1260539Notes

Reaction equation

HRID 1260539 reaction equation
[OH:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(OCC)(=O)C>CN1C(=O)CCC1.O>[CH2:29]([N:7]1[C:2](=[O:1])[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:11][CH:10]=2)=[CH:6]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 178474734HCID 178474734, compound

Product 1

HCID 67071797HCID 67071797, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

N-{3-[4-(6-Hydroxypyridin-3-yloxy)phenyl]-1-methylpropyl}acetamide (150 mg, 0.5 mmol) was stirred with potassium tert-butoxide (168 mg, 1.5 mmol) and benzylbromide (342 mg, 2 mmol) in 3 ml of NMP at room temperature for 10 h. The batch was admixed with ethyl acetate and water, and the organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 22 mg (11%), M+H+: 391.15. N-{3-[4-(1-Benzyl-6-oxo-1,6-dihydropyridin-3-yloxy)phenyl]-1-methylpropyl}acetamide was obtained as by-product.

Workup

  1. customthe organic phase was separated off
  2. concentrationconcentrated
  3. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-4a2aca712674430fa831878a4e164174
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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