Butyl bromide → HCID 178448422, compound

HRID 1028188Notes

Reaction equation

HRID 1028188 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([CH:19]=1)[C:7]([NH:9][C:10]1[S:11][C:12]2[O:18][CH2:17][CH2:16][CH2:15][C:13]=2[N:14]=1)=[O:8].CC(C)([O-])C.[K+].Br[CH2:29][CH2:30][CH2:31][CH3:32]>CN(C)C=O.O1CCCC1>[CH2:29]([N:14]1[C:13]2[CH2:15][CH2:16][CH2:17][O:18][C:12]=2[S:11]/[C:10]/1=[N:9]\[C:7](=[O:8])[C:6]1[CH:19]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[O:20][CH3:21])[CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 23665647Potassium tert-butoxideHCID 86624876HCID 86624876, compound

Product 1

HCID 178448422HCID 178448422, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the product from Example 26B (mixture) in 10 mL of N,N-dimethylformamide and tetrahydrofuran (1:4) were added potassium t-butoxide (21 mg, 0.18 mmol) and 1-bromobutane (25 mg, 0.18 mmol). After stirring at 80° C. for 16 h, the reaction mixture was cooled to room temperature and quenched with saturated aqueous NaHCO3 (10 mL). The aqueous layer was extracted with ethyl acetate (3×20 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, 0-50% ethyl acetate in methylene chloride) to afford 3 mg of the title compound as a single regioisomer. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.94 (t, J=7.3 Hz, 3H), 1.28-1.42 (m, 2H), 1.73 (t, 2H), 2.06 (t, 2H), 2.67 (t, J=6.3 Hz, 2H), 3.79 (s, 3H), 4.06-4.13 (m, 2H), 4.18-4.25 (m, 2H), 7.11 (d, J=8.8 Hz, 1H), 7.45 (dd, J=8.8, 3.1 Hz, 1H), 7.71 (d, J=3.1 Hz, 1H); MS (ESI+) m/z 381 (M+H)+.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customquenched with saturated aqueous NaHCO3 (10 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×20 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-fe00a9e385394bc6800a857168e52766
Source dataset
uspto-grants-2014_05
Patent number
US08735434B2

Reaction notes

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