Trifluoroacetic acid → HCID 24871780, compound

HRID 1259471Notes

Reaction equation

HRID 1259471 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(O)(=O)C.C(O)(=O)C.[I:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1.[C:23]1([O:29][CH3:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[CH3:30][O:29][C:23]1[CH:28]=[CH:27][C:26]([I+:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86654449HCID 86654449, compound

Product 1

HCID 24871780HCID 24871780, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.15 mL, 2 mmol) was added dropwise to a stirred solution of 3-iodopyridine diacetate (0.23 g, 1 mmol) in dichloromethane at −40° C. and stirred for 0.5 h when the solution was allowed to warm to room temperature for 1 h after which time it was re-cooled to −40° C. and anisole (0.11 mL, 1 mmol) added dropwise and the reaction mixture allowed to warm to room temperature overnight. The reaction mixture was concentrated in vacuo to give a light brown oil. Crystallisation gave the title compound as a colourless crystalline solid (0.22 g, 0.52 mmol, 52%); mp 150-151° C. (from DCM-ether) silica gel TLC Rf 0.20 (9:2 DCM-MeOH); (Found C, 39.67; H, 2.53; N, 3.21. C14H11F31NO3 requires C, 39.55; H, 2.61; N, 3.29%.); νmax/cm−1 (neat) 3050, 1642, 1570, 1251, 1177, 1130; δH (300 MHz; d6-acetone) 8.93 (1H, d, H2 J 2 Hz), 8.74 (1H, d, H6, J 4 Hz), 8.39 (1H, dt, H4 J 5, 2 Hz), 7.91 (2H, d, H2′/H6′ J 5 Hz), 7.38 (1H, dd, H5 J 5, 3 Hz), 6.93 (2H, d, H3′/H5′ J 5 Hz), 3.84 (3H, s, OMe); δC (75 MHz; d6-Acetone) 163.99 (C4′), 154.59 (C2), 152.76 (C6), 143.06 (C4), 138.63 (C2′/C6′), 127.45 (C5), 118.68 (C3′/C5′), 116.64 (C1′), 107.60 (C3), 56.51 (OMe); m/z (ES) 312 (M+, 100%), 185 (20). [Found: M+], 311.9878.

Workup

  1. temperaturewas re-cooled to −40° C.
  2. temperatureto warm to room temperature overnight
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto give a light brown oil
  5. customCrystallisation

Sources & evidence

ORD record
ord-862b40f1f1374641ae34e295a40ee31a
Source dataset
uspto-grants-2013_06
Patent number
US08466313B2

Reaction notes

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