2-(Bromomethyl)-6-methylpyridine → 5-(4-chlorophenyl)-N-((6-methylpyridin-2-yl)methyl)-N-(4-(piperazin-1-yl)phenyl)furan-2-carboxamide

HRID 273573Notes

Reaction equation

HRID 273573 reaction equation
Cc1cccc(CBr)n1.CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(Cl)cc4)o3)cc2)CC1>O=S(=O)(O)O.CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1.CN(C)C=O.CN(C)C=O.CN(C)C=O.COCCOCCOC>CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(Cl)cc4)o3)cc2)CC1.CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(Cl)cc4)o3)cc2)CC1.Cc1cccc(CN(C(=O)c2ccc(-c3ccc(Cl)cc3)o2)c2ccc(N3CCNCC3)cc2)n1

Participants

8

Reactant 2

HCID 125437332-(Bromomethyl)-6-methylpyridineHCID 168301698t-Butyl 4-(4-(5-(4-chlorophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate

Product 2

HCID 168301698t-Butyl 4-(4-(5-(4-chlorophenyl)furan-2-carboxamido)phenyl)piperazine-1-carboxylate2×HCID 1683017065-(4-chlorophenyl)-N-((6-methylpyridin-2-yl)methyl)-N-(4-(piperazin-1-yl)phenyl)furan-2-carboxamideYield 167%

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidReagentHCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneReagentHCID 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-5ccfba420b7b4bf89d51d7718f8da610
Source dataset
Cernak miniaturized N-alkylation with BOC deprotection
Original link
View source

Reaction notes

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