Acetic Acid → HCID 68712206, compound

HRID 1820129Notes

Reaction equation

HRID 1820129 reaction equation
C(O)(=O)C.[Br:5][C:6]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[C:8]([C:15]([F:18])([F:17])[F:16])[C:7]=1[NH:19][C:20](=[O:29])[CH2:21][CH2:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>O1CCCC1.[Zn]>[NH2:12][C:10]1[CH:9]=[C:8]([C:15]([F:17])([F:18])[F:16])[C:7]([NH:19][C:20](=[O:29])[CH2:21][CH2:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[C:6]([Br:5])[CH:11]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 68712047HCID 68712047, compound

Product 1

HCID 68712206HCID 68712206, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Acetic acid (3.70 mL) was added slowly to a mixture of zinc dust (7.88 g) and N-(2-bromo-4-nitro-6-trifluoromethyl-phenyl)-3-cyclohexyl-propionamide (1.99 g) in tetrahydrofuran (40 mL). The reaction mixture was then stirred for 1½ hours at 25° C. The reaction mixture was filtered, diluted with saturated aqueous sodium bicarbonate (400 mL) and extracted with ethyl acetate (3×100 mL). The combined organic phases were washed with water (100 mL), brine (100 mL), dried over sodium sulfate and concentrated in vacuo to furnish 1.85 g (100% yield) of the title compound as a yellow solid. LC-MS (m/z) 394 (MH+); tR=3.22, (UV, ELSD) 92%, 99%. 1H NMR (500 MHz, DMSO-d6): 0.86 (q, 2H), 1.17 (m, 3H), 1.26 (m, 1H), 1.46 (q, 2H), 1.67 (m, 5H), 2.40 (t, 2H), 5.83 (s, 2H), 6.88 (d, 1H), 7.07 (d, 1H), 9.27 (s, 1H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additiondiluted with saturated aqueous sodium bicarbonate (400 mL)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined organic phases were washed with water (100 mL), brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8dcd0b5b8fd040099d759bb66c703f44
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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