2-(Bromomethyl)pyridine → HCID 57393087, compound

HRID 273615Notes

Reaction equation

HRID 273615 reaction equation
BrCc1ccccn1.CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(C#N)cc4)o3)cc2)CC1>O=S(=O)(O)O.[Li]N([Si](C)(C)C)[Si](C)(C)C.CN(C)C=O.CN(C)C=O.CN(C)C=O.COCCOCCOC>N#Cc1ccc(-c2ccc(C(=O)N(Cc3ccccn3)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 5642092-(Bromomethyl)pyridineHCID 168301699Tert-butyl 4-(4-(5-(4-cyanophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate

Product 2

HCID 57393087HCID 57393087, compoundYield 48%HCID 168301699Tert-butyl 4-(4-(5-(4-cyanophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate2×

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidReagentHCID 178418261HCID 178418261, compoundReagentHCID 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-49c6a30fb5a04e9780dbbbfc2701dbb8
Source dataset
Cernak miniaturized N-alkylation with BOC deprotection
Original link
View source

Reaction notes

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