4-Fluorobenzyl bromide → HCID 58392804, compound

HRID 446843Notes

Reaction equation

HRID 446843 reaction equation
Cl.[F:2][C@@:3]12[C@:16]3([CH3:17])[C:11](=[CH:12][C:13](=[O:18])[CH:14]=[CH:15]3)[C@@H:10]([F:19])[CH2:9][C@H:8]1[C@@H:7]1[CH2:20][C@@H:21]3[C@:25]([C:26](=[O:29])[CH2:27][F:28])([C@@:6]1([CH3:30])[CH2:5][C@@H:4]2[OH:31])[CH2:24][NH:23][CH2:22]3.[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Br)=[CH:35][CH:34]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:2][C@@:3]12[C@:16]3([CH3:17])[C:11](=[CH:12][C:13](=[O:18])[CH:14]=[CH:15]3)[C@@H:10]([F:19])[CH2:9][C@H:8]1[C@@H:7]1[CH2:20][C@@H:21]3[C@:25]([C:26](=[O:29])[CH2:27][F:28])([C@@:6]1([CH3:30])[CH2:5][C@@H:4]2[OH:31])[CH2:24][N:23]([CH2:37][C:36]1[CH:39]=[CH:40][C:33]([F:32])=[CH:34][CH:35]=1)[CH2:22]3

Participants

5

Reactant 3

HCID 680214-Fluorobenzyl bromideHCID 516892Sodium BicarbonateHCID 86656548HCID 86656548, compound

Product 1

HCID 58392804HCID 58392804, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of compound 166 (145 mg, 0.315 mmol), 4-fluorobenzylbromide (0.059 ml, 0.473 mmol) and TEA (0.132 ml, 0.946 mmol) in DCM (10 ml) is stirred at RT overnight. The mixture is diluted with DCM and treated with 5% NaHCO3. The organic phase is then washed with brine, dried over Na2SO4 and filtered. The solvent is evaporated and the crude is purified by silica gel flash chromatography (eluent DCM(AcOEt 7/3 to 1/1) to yield a solid that is triturated in Et2O. Title compound (54 mg, 32.2% yield) is recovered by filtration.

Workup

  1. washThe organic phase is then washed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customThe solvent is evaporated
  5. customthe crude is purified by silica gel flash chromatography (eluent DCM(AcOEt 7/3 to 1/1)
  6. customto yield a solid
  7. customthat is triturated in Et2O

Sources & evidence

ORD record
ord-6bfb17537e8641d69ee5abd8c7dba10a
Source dataset
uspto-grants-2013_07
Patent number
US08481517B2

Reaction notes

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