Benzyl Bromide → HCID 66720430, compound

HRID 1644562Notes

Reaction equation

HRID 1644562 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:37])=[C:11]([N:14]4[CH2:19][CH2:18][CH:17]([CH2:20][O:21][C:22]5[CH:27]=[CH:26][C:25]([N:28]6[CH2:32][C@H:31]([CH2:33][OH:34])[O:30][C:29]6=[O:35])=[CH:24][C:23]=5[F:36])[CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:38])[C:6]([C:39]([OH:41])=[O:40])=[CH:5]2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[CH:48]1[CH:53]=[CH:52][C:51]([CH2:54]Br)=[CH:50][CH:49]=1>CN(C=O)C>[CH2:54]([O:40][C:39]([C:6]1[C:7](=[O:38])[C:8]2[C:13](=[CH:12][C:11]([N:14]3[CH2:15][CH2:16][CH:17]([CH2:20][O:21][C:22]4[CH:27]=[CH:26][C:25]([N:28]5[CH2:32][C@H:31]([CH2:33][OH:34])[O:30][C:29]5=[O:35])=[CH:24][C:23]=4[F:36])[CH2:18][CH2:19]3)=[C:10]([F:37])[CH:9]=2)[N:4]([CH:1]2[CH2:3][CH2:2]2)[CH:5]=1)=[O:41])[C:51]1[CH:52]=[CH:53][CH:48]=[CH:49][CH:50]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 24858263HCID 24858263, compound

Product 1

HCID 66720430HCID 66720430, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of the compound of Example 2 (600 mg) in DMF (10 mL) was treated with K2CO3 (155 mg) and BnBr (160 μl) and stirred at 80° C. for 24 h. The solvent was evaporated under reduced pressure and the residue was worked up (DCM). The residue was stirred in ether (100 mL) and the resulting crystals were collected by filtration affording 612 mg (90.6% yield) of an off-white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. stirringThe residue was stirred in ether (100 mL)
  3. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-28b7047afd354e588a7f480c92cd281b
Source dataset
uspto-grants-2012_02
Patent number
US08124623B2

Reaction notes

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