2-(Bromomethyl)pyridine → HCID 178509568, compound

HRID 273618Notes

Reaction equation

HRID 273618 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.CC(C)(C)[O-].[Na+].CN(C)C=O.CN(C)C=O.CN(C)C=O.COCCOCCOC>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.N#Cc1ccc(-c2ccc(C(=O)N(Cc3ccncc3)c3ccc(N4CCNCC4)cc3)o2)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 168301699Tert-butyl 4-(4-(5-(4-cyanophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate2×HCID 178509568HCID 178509568, compoundYield 93%

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-e1930653897b4b25962bb1b8e76ba437
Source dataset
Cernak miniaturized N-alkylation with BOC deprotection
Original link
View source

Reaction notes

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