Methyl triflate → HCID 22481060, compound

HRID 2182821Notes

Reaction equation

HRID 2182821 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[N:12]([CH3:13])[CH:11]=[C:10]([C:14]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[O:15])[CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[O:24](C)[S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26]>C(Cl)Cl>[OH2:7].[F:29][C:28]([F:31])([F:30])[S:25]([O-:27])(=[O:26])=[O:24].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[N:12]([CH3:13])[CH:11]=[C:10]([C:14]([C:16]3[CH:21]=[CH:20][N+:19]([CH3:28])=[CH:18][CH:17]=3)=[O:15])[CH:9]=2)=[O:7])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 10149810HCID 10149810, compound

Product 1

HCID 22481060HCID 22481060, compoundYield 149.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.64 g (2 mmol) of [5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]pyridin-4-ylmethanone and 0.22 mL (2 mmol) methyl triflate was stirred for 16 h in 20 mL of CH2Cl2. The solvent was evaporated and the residue recrystallized from EtOAc to give 0.76 g (77% yield) of the title compound as a white solid: mp 113-114° C. ES-MS m/z=339 (M++H). 1H NMR (300 MHz, CDCl3) δ 4.0 (s, 3H); 4.55 (s, 3H), 7.32 (dd, 2H); 7.8 (m, 3H); 8.2 (dd, 2H); 9.0 (dd, 2H). Anal calc'd for: C19H16ClN2O2.CF3O3S. 0.2 H2O: C, 48.77; H, 3.35; N, 5.68; KF,0.73. Found: C, 48.91; H, 3.5; N, 5.57; KF,1.03.

Workup

  1. customThe solvent was evaporated
  2. customthe residue recrystallized from EtOAc

Sources & evidence

ORD record
ord-f44ee3521185406a948dd3a8ca073e29
Source dataset
uspto-grants-2005_05
Patent number
US06897319B2

Reaction notes

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