Sodium ethoxide → HCID 66920811, compound

HRID 1364547Notes

Reaction equation

HRID 1364547 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:4]=1[CH2:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Br)[N:10]=1)=[O:8].[CH3:22][CH2:23][O-:24].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:4]=1[CH2:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:24][CH2:23][CH3:22])[N:10]=1)=[O:8]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 86606904HCID 86606904, compound

Product 1

HCID 66920811HCID 66920811, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of bromide from Example 156A (35 mg, 0.1 mmol) and NaOEt (21% w/w ethanol soulution, 56 μL, 0.15 mmol) in ethanol (500 μL) was heated in a microwave oven at 150° C. for 10 minutes. It was partitioned between ethyl acetate and water. The organic phase was dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography on silica gel column using ethyl acetate:hexane (1:1) to provide the titled compound (22 mg, 70%). MS (ESI(+)) m/e 317 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 8.89 (t, J=6.4 Hz, 1H), 7.89-7.84 (m, 1H), 7.63-7.60 (m, 1H), 7.02-6.74 (m, 4H), 4.46 (d, J=6.4 Hz, 2H), 4.45 (q, J=7.1 Hz, 2H), 3.80 (s, 3H), 3.65 (s, 3H), 1.35 (t, J=7.1 Hz, 3H).

Workup

  1. customIt was partitioned between ethyl acetate and water
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel column

Sources & evidence

ORD record
ord-ae132e9f20054870b92249b9051b6056
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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