Benzyl Bromide → HCID 86711835, compound

HRID 623747Notes

Reaction equation

HRID 623747 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH3:13])=[CH:11][NH:10][C:9]=2[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH2:21]([N:10]1[CH:11]=[C:12]([CH3:13])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[C:9]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86711834HCID 86711834, compound

Product 1

HCID 86711835HCID 86711835, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 3-(4-fluorophenyl)-4-methyl-1H-pyrrole-2-carboxylate (5.5 g, 22.26 mmol) in DMF (12 mL) was added to a mixture of 60% NaH (1.1 g, 33.39 mmol) in dry DMF (20 mL) at 0° C. under a N2 atmosphere and the mixture was stirred for 15 min. Benzyl bromide (2.9 mL, 24.49 mmol) was added and it was stirred at 80° C. for 12 h. The reaction mixture was cooled to 0° C., quenched with brine (20 mL), diluted with water (50 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (75 mL) and brine (75 mL), dried (Na2SO4) and concentrated under reduced pressure to afford the desired product (6.5 g, 87%) as brown color solid.

Workup

  1. stirringit was stirred at 80° C. for 12 h
  2. customquenched with brine (20 mL)
  3. additiondiluted with water (50 mL)
  4. extractionextracted with EtOAc (3×50 mL)
  5. washThe combined organic layers were washed with water (75 mL) and brine (75 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8964e0d84f0e4cf8bd8c95183cf2f8e1
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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