2-(Bromomethyl)-6-methylpyridine → HCID 57401826, compound

HRID 273623Notes

Reaction equation

HRID 273623 reaction equation
Cc1cccc(CBr)n1.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>Cc1cccc(CN(C(=O)c2ccc(-c3ccc(C#N)cc3)o2)c2ccc(N3CCNCC3)cc2)n1.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 125437332-(Bromomethyl)-6-methylpyridineHCID 168301699Tert-butyl 4-(4-(5-(4-cyanophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate

Product 2

HCID 57401826HCID 57401826, compoundYield 57%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-05b90f2231ff49d89d874ea017daa614
Source dataset
Cernak miniaturized N-alkylation with BOC deprotection
Original link
View source

Reaction notes

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