Ethyl Bromide → HCID 66753310, compound

HRID 1896328Notes

Reaction equation

HRID 1896328 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](=[O:14])[N:12]3[CH:15]=[CH:16][S:17][C:11]3=[N:10][C:9]=2[CH3:18])=[CH:4][CH:3]=1.[CH2:19](Br)[CH3:20].[H-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH2:19]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13](=[O:14])[N:12]3[CH:15]=[CH:16][S:17][C:11]3=[N:10][C:9]=2[CH3:18])=[CH:6][CH:7]=1)[CH3:20]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 66753136HCID 66753136, compound

Product 1

HCID 66753310HCID 66753310, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of Step 1 intermediate (250 mg, 0.967 mmol) in DMF (4 ml) was added ethyl bromide (0.147 g, 1.355 mmol) and NaH (0.053 g, 1.355 mmol) and heated to 80° C. for 15.0 h. After completion of the reaction, the mixture was diluted with ethyl acetate, washed with water, brine, dried over anhydrous Na2SO4 to afford 300 mg of the desired compound as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.34 (t, J=6.6 Hz, 3H), 2.17 (s, 3H), 4.05 (q, J=6.6 Hz, 2H), 6.93-6.96 (m, 2H), 7.17-7.20 (m, 2H), 7.50 (d, J=4.5 Hz, 1H), 7.98 (d, J=4.8 Hz, 1H); ESI-MS (m/z) 311.28 (M+H)+.

Workup

  1. customAfter completion of the reaction
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-3515867aa5794da3b6a057d9f3aa2bae
Source dataset
uspto-grants-2013_08
Patent number
US08518955B2

Reaction notes

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