2-Bromoethanol → HCID 59846150, compound

HRID 605001Notes

Reaction equation

HRID 605001 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:18](=[O:28])[NH:17][CH:16]=[CH:15][C:14]=3[N:13]=2)=[CH:8][CH:7]=1)(=O)C.[H-].[Na+].Br[CH2:32][CH2:33][OH:34]>CN(C=O)C.C(OCC)(=O)C.O>[OH:34][CH2:33][CH2:32][N:17]1[CH:16]=[CH:15][C:14]2[N:13]=[C:12]([C:9]3[CH:8]=[CH:7][C:6]([CH2:5][OH:4])=[CH:11][CH:10]=3)[C:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:20][C:19]=2[C:18]1=[O:28]

Participants

7

Reactant 3

HCID 108982-Bromoethanol2×HCID 24758Sodium hydrideHCID 67055583HCID 67055583, compound

Product 1

HCID 59846150HCID 59846150, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(5-oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzyl acetate (see preparation of 3-4 for this intermediate) (74 mg, 0.20 mmol) in dry DMF (1 mL) was added 60% sodium hydride in mineral oil (57 mg, 1.4 mmol). After 10 minutes 2-bromoethanol (50 μL, 0.71 mmol) was added to the reaction which was monitored over 24 hours by LC/MS. Two more portions of 2-bromoethanol were added during this period. The reaction was diluted with ethyl acetate and water. After stirring for 0.5 hour, the organic layer was isolated and washed with aqueous NaHCO3, dried (anhydrous Na2SO4), filtered and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with 30-100% ethyl acetate and then 0.25-1.5% methanol/ethyl acetate (sat'd with NH3) to give the title compound. 1H-NMR (500 MHz, CDCl3): δ 8.68 (1H, s), 7.47 (1H, d, J=7.8 Hz), 7.39 (2H, d, J=8 Hz), 7.27-7.31 (5H, m), 7.20-7.22 (2H, m), 6.89 (1H, d, J=7.5 Hz), 4.65 (2H, s) 4.19 (2H, t, J=5.3 Hz), 3.94 (2H, t, J=5.3 Hz) m/e (m+1): 373.2.

Workup

  1. customthe organic layer was isolated
  2. washwashed with aqueous NaHCO3
  3. dry with materialdried (anhydrous Na2SO4)
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with 30-100% ethyl acetate

Sources & evidence

ORD record
ord-c9aeb2454dce494ab9a5ab7d9e0c27a4
Source dataset
uspto-grants-2011_03
Patent number
US07910561B2

Reaction notes

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