Allyl bromide → HCID 178440464, compound

HRID 2110570Notes

Reaction equation

HRID 2110570 reaction equation
[In].[CH2:2](Br)[CH:3]=[CH2:4].[CH3:6][O:7][N:8]=[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[CH:11]=[C:10]1[OH:20]>CN(C)C=O>[CH2:4]([C:9]1([NH:8][O:7][CH3:6])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[CH:11]=[C:10]1[OH:20])[CH:3]=[CH2:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 5359967Indium2×HCID 178502624HCID 178502624, compound

Product 1

HCID 178440464HCID 178440464, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of indium powder (0.68 g, 5.9 mmol) in anhydrous N,N-dimethylformamide (2 mL) at 0° C. was added allylbromide (0.76 mL, 8.8 mmol) dropwise over 5 min. The cooling bath was removed and the resulting exothermic reaction was allowed to stir for several minutes, during which time the indium metal dissolved. The resulting solution was cooled to 0° C., and a solution of Example 7A (1.00 g, 4.9 mmol) in anhydrous N,N-dimethylformamide (8 mL) was added. The resulting solution was allowed to warm to rt and stirred 1 h. The reaction mixture was partitioned between H2O (50 mL) and ethyl acetate (3×50 mL), and the combined organic layers were dried over Na2SO4. The solution was filtered and concentrated, and the product was precipitated from diethyl ether to provide the title compound as a light tan powder (0.99 g, 82%). 1H NMR (300 MHz, DMSO-d6) δ ppm 11.84 (s, 1H), 7.85 (d, J=7.7 Hz, 2H), 7.60 (t, J=7.4 Hz, 1H), 7.32-7.48 (m, 1H), 7.14 (br s, 1H), 5.68 (br s, 1H), 5.09 (m, 1H), 4.64-4.81 (m, 2H), 3.11 (s, 3H), 2.20-2.45 (m, 2H).

Workup

  1. customThe cooling bath was removed
  2. customthe resulting exothermic reaction
  3. dissolutiondissolved
  4. temperatureto warm to rt
  5. customThe reaction mixture was partitioned between H2O (50 mL) and ethyl acetate (3×50 mL)
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. filtrationThe solution was filtered
  8. concentrationconcentrated
  9. customthe product was precipitated from diethyl ether

Sources & evidence

ORD record
ord-80183b10fd9e4ddb937dafd7efc6fcca
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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