Iodoethane → HCID 70980817, compound

HRID 1749083Notes

Reaction equation

HRID 1749083 reaction equation
[C:1]([O:5][C:6](=[O:37])[N:7]([C:19]1[CH:20]=[CH:21][C:22]2[N:27]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[C:26](=[O:35])[CH2:25][O:24][C:23]=2[N:36]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[O:17][CH3:18])([CH3:4])([CH3:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.I[CH2:49][CH3:50].[CH2:51]1COC[CH2:52]1>>[C:1]([O:5][C:6](=[O:37])[N:7]([C:19]1[CH:20]=[CH:21][C:22]2[N:27]([C:28]3[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=3)[C:26](=[O:35])[C:25]([CH2:49][CH3:50])([CH2:51][CH3:52])[O:24][C:23]=2[N:36]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[O:17][CH3:18])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 6340IodoethaneHCID 8028TetrahydrofuranHCID 2733832Lithium HexamethyldisilazideHCID 70980339HCID 70980339, compound

Product 1

HCID 70980817HCID 70980817, compound

Conditions

Temperature
-78 °C

Procedure

[1-(4-Chloro-phenyl)-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl]-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester (370 mg, 0.66 mmol) was dissolved in THF (8 mL) and cooled to −78° C. LiHMDS (1 M solution in THF, 2 mL, 1.98 mmol) was added and the mixture stirred at −78° C. for 15 minutes. Iodoethane (160 mL, 1.98 mmol) was then added to the mixture, the cooling bath removed and then stirring continued for a further 15 minutes, during which time, the mixture reached ambient temperature. Saturated aqueous ammonium chloride and EtOAc were added. The EtOAc layer was isolated and washed with dilute aqueous potassium hydrogen phosphate solution. The EtOAc layer was then washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified using SiO2 chromatography (10-30% EtOAc/Petrol) to give [1-(4-chloro-phenyl)-3,3-diethyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl]-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester (145 mg). MS: [M+H]+ 582.

Workup

  1. customthe cooling bath removed
  2. stirringstirring
  3. waitcontinued for a further 15 minutes, during which time
  4. customreached ambient temperature
  5. additionSaturated aqueous ammonium chloride and EtOAc were added
  6. customThe EtOAc layer was isolated
  7. washwashed with dilute aqueous potassium hydrogen phosphate solution
  8. washThe EtOAc layer was then washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified

Sources & evidence

ORD record
ord-314ef369d3fd407d9e093984061cdbd6
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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