Iodine → HCID 71254909, compound

HRID 1507628Notes

Reaction equation

HRID 1507628 reaction equation
C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.[F:29][C:30]1[CH:35]=[CH:34][C:33]([C:36](=[O:50])[CH:37]([NH:43][C:44](=O)[C:45]([F:48])([F:47])[F:46])[C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:32][CH:31]=1>C(Cl)Cl>[F:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]2[O:50][C:44]([C:45]([F:46])([F:47])[F:48])=[N:43][C:37]=2[C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86729692HCID 86729692, compound

Product 1

HCID 71254909HCID 71254909, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (64 mL, 0.46 mmol)) was added to a solution of triphenylphosphine (60 mg, 0.23 mmol) and iodine (58 mg, 0.23 mmol) in dry DCM (0.5 mL) and stirred for 5 min. Then a solution of ethyl 3-(4-fluorophenyl)-3-oxo-2-(2,2,2-trifluoroacetamido)propanoate (37 mg, 12 mmol) in dry DCM (0.7 mL) was added and the reaction mixture was stirred for 1 hr. The solvent was removed under reduced pressure, and the residue was purified by SiO2 chromatography on silica gel (isocratic DCM) to yield a white solid (31 mg, 88% yield). 1HNMR (400 MHz, CDCl3): d 8.12 (m, 2H), 7.18 (t, 2H, J=8.8 Hz), 4.43 (q, 2H, J=7.2 Hz), 1.39 (t, 3H, J=7.2 Hz). 19FNMR (400 MHz, CDCl3): d −66.10, −107.21. MS (ESI): m/z MS (ESI): m/z 303.9 [M+H]+

Workup

  1. stirringthe reaction mixture was stirred for 1 hr
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by SiO2 chromatography on silica gel (isocratic DCM)

Sources & evidence

ORD record
ord-4a0a9c5128f24f078dbb392c5651dae0
Source dataset
uspto-grants-2015_12
Patent number
US09221805B2

Reaction notes

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