Sodium hydride → HCID 14462625, compound
Reaction equation
ClC1C=C(C=CC=1)C[N:6]1[CH:10]=[C:9]([CH3:11])[C:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:7]1[C:19]([O:21][CH2:22][CH3:23])=[O:20].[H-].[Na+].ClC1C=C(C=CC=1)CBr>CN(C=O)C>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:8]2[C:9]([CH3:11])=[CH:10][NH:6][C:7]=2[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:14]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of ethyl 1-(3-chlorobenzyl)-3-(4-chlorophenyl)-4-methyl-1H-pyrrole-2-carboxylate (1 g, 3.79 mmol) in dry DMF (5 mL) was added dropwise to a cooled suspension of 60% NaH in mineral oil (0.167 g, 4.17 mmol) in dry DMF (5 mL). The mixture was stirred at 0° C. for 20 min, then 3-chlorobenzyl bromide (0.524 mL, 3.98 mmol) was added dropwise over 5 min. The mixture was stirred for 10 min at 0° C., then the cooling was removed and the stirring was continued for 2.5 h at room temperature. The reaction was quenched by the addition of saturated aqueous NH4Cl/ice (1:1, 50 mL) and the product was extracted with EtOAc (50 mL). The combined organic layers were dried on Na2SO4 and evaporated and the residual crude product purified using gravity column chromatography (silica, heptane/EtOAc 9:1) to give the desired product (1.18 g, 80%).
Workup
- stirringThe mixture was stirred for 10 min at 0° C.
- customthe cooling was removed
- waitthe stirring was continued for 2.5 h at room temperature
- customThe reaction was quenched by the addition of saturated aqueous NH4Cl/ice (1:1, 50 mL)
- extractionthe product was extracted with EtOAc (50 mL)
- customThe combined organic layers were dried on Na2SO4
- customevaporated
- customthe residual crude product purified
Sources & evidence
- ORD record
- ord-0293a7df2e5242448a26736431845f41
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09302988B2
Reaction notes
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