2-Bromoethyl methyl ether → HCID 178495812, compound

HRID 1470032Notes

Reaction equation

HRID 1470032 reaction equation
[C:1]([C:3]1[S:7][C:6]([NH:8][C:9]([C:11]23[CH2:20][CH:15]4[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]4)[CH2:12]2)[CH2:18]3)=[O:10])=[N:5][CH:4]=1)#[N:2].CC(C)([O-])C.[K+].[CH3:27][O:28][CH2:29][CH2:30]Br>CN(C)C=O.O1CCCC1>[C:1]([C:3]1[S:7]/[C:6](=[N:8]\[C:9]([C:11]23[CH2:20][CH:15]4[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]4)[CH2:12]2)[CH2:18]3)=[O:10])/[N:5]([CH2:30][CH2:29][O:28][CH3:27])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 809722-Bromoethyl methyl etherHCID 23665647Potassium tert-butoxideHCID 87181583HCID 87181583, compound

Product 1

HCID 178495812HCID 178495812, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of Example 183B (240 mg, 0.84 mmol) in N,N-dimethylformamide/tetrahydrofuran (1:4, 10 mL) were added a solution of potassium tert-butoxide (Aldrich, 133 mg, 1.2 mmol) and commercially available, 2-bromoethyl methyl ether (Aldrich, 104 μL, 1.2 mmol). The reaction mixture was stirred at 80° C. for 16 hours, cooled to room temperature, quenched with saturated aqueous NaHCO3 (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% ethyl acetate in hexanes) to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 1.59-1.77 (m, 6H), 1.84-1.91 (m, 6H), 1.95-2.04 (m, 3H), 3.26 (s, 3H), 3.71 (t, J=5.3 Hz, 2H), 4.36 (t, J=5.1 Hz, 2H), 8.54 (s, 1H); MS (ESI+) m/z 346 (M+H)+; Anal. Calculated for C18H23N3O2S: C, 62.58; H, 6.71; N, 12.16. Found: C, 62.15; H, 6.89; N, 11.95.

Workup

  1. temperaturecooled to room temperature
  2. customquenched with saturated aqueous NaHCO3 (10 mL)
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9ade8e3ffea747da9e2cd14bff133075
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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