(3-Bromopropyl)benzene → HCID 18784732, compound

HRID 1599043Notes

Reaction equation

HRID 1599043 reaction equation
[H-].[Na+].[C:3]1([CH:9]([O:32][CH2:33]C2C=CC=CC=2)[C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][CH:19]([N:22]4[CH2:30][C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[C:23]4=[O:31])[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.BrC[CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CN(C=O)C>[C:3]1([CH:9]([O:32][CH2:33][CH2:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][CH:19]([N:22]4[CH2:30][C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[C:23]4=[O:31])[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 12503(3-Bromopropyl)benzeneHCID 24758Sodium hydrideHCID 18784744HCID 18784744, compound

Product 1

HCID 18784732HCID 18784732, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (44 mg, 1.1 mmol) in DMF (5 mL) at 0° C. was added dropwise a solution of Example 293 Part A compound (400 mg, 1.0 mmol) in DMF (1 mL). The reaction was stirred at 0° C. for 30 min. 1-Bromo-3-phenylpropane (219 mg, 1.1 mmol) was added dropwise to the reaction at 0° C. The reaction was stirred at 0° C. for 1 h then warmed to RT overnight. The reaction was quenched with saturated ammonium chloride solution (2 mL). Ethyl acetate (100 mL) was added to the reaction, and the organic layer was washed with water (2×30 mL), brine (2×30 mL) and dried over MgSO4. Purification was performed by flash chromatography on silica gel (100 g), loaded and eluted with 50% ethyl acetate in hexane. Pure fractions were combined and evaporated to give title compound (335 mg, 65%) as a white solid.

Workup

  1. stirringThe reaction was stirred at 0° C. for 1 h
  2. temperaturethen warmed to RT overnight
  3. customThe reaction was quenched with saturated ammonium chloride solution (2 mL)
  4. additionEthyl acetate (100 mL) was added to the reaction
  5. washthe organic layer was washed with water (2×30 mL), brine (2×30 mL)
  6. dry with materialdried over MgSO4
  7. customPurification
  8. washeluted with 50% ethyl acetate in hexane
  9. customevaporated

Sources & evidence

ORD record
ord-a4c1aa4e31eb4420b416cf3e2bda9a0e
Source dataset
uspto-grants-1998_04
Patent number
US05739135

Reaction notes

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