1-(Bromomethyl)-2-phenylbenzene → HCID 57394816, compound

HRID 273626Notes

Reaction equation

HRID 273626 reaction equation
BrCc1ccccc1-c1ccccc1.CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(C#N)cc4)o3)cc2)CC1>O=S(=O)(O)O.CC(C)(C)[O-].[Na+].CN(C)C=O.CN(C)C=O.CN(C)C=O.COCCOCCOC>N#Cc1ccc(-c2ccc(C(=O)N(Cc3ccccc3-c3ccccc3)c3ccc(N4CCNCC4)cc3)o2)cc1.CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(C#N)cc4)o3)cc2)CC1.CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(C#N)cc4)o3)cc2)CC1

Participants

8

Reactant 2

HCID 2633651-(Bromomethyl)-2-phenylbenzeneHCID 168301699Tert-butyl 4-(4-(5-(4-cyanophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate

Product 2

HCID 57394816HCID 57394816, compoundYield 26%HCID 168301699Tert-butyl 4-(4-(5-(4-cyanophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate2×

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidReagentHCID 23676156Sodium t-butoxideReagentHCID 6228DimethylformamideSolvent3×HCID 8150DiglymeSolvent

Conditions

Temperature
23 °C

Workup

  1. additionquenched by addition of saturated aqueous NaHCO3 (2 uL) and diluted with water (1 uL) and DMSO (2 uL)
  2. additionquenched by addition of saturated aqueous NaHCO3 (2 uL) and diluted with water (1 uL) and DMSO (2 uL)
  3. additionquenched by addition of saturated aqueous NaHCO3 (2 uL) and diluted with water (1 uL) and DMSO (2 uL)
  4. additionThe reactions were further diluted to 10 mM using DMSO.

Sources & evidence

ORD record
ord-5824de374aea4978855a33e3dc671946
Source dataset
Cernak miniaturized N-alkylation with BOC deprotection
Original link
View source

Reaction notes

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