Triethylamine → 2-fluoro-3-iodo-N-(3-isopropoxyphenyl)-4-methylbenzamide

HRID 1668934Notes

Reaction equation

HRID 1668934 reaction equation
C(Cl)(=O)C(Cl)=O.[F:7][C:8]1[C:16]([I:17])=[C:15]([CH3:18])[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O.[CH:19]([O:22][C:23]1[CH:24]=[C:25]([NH2:29])[CH:26]=[CH:27][CH:28]=1)([CH3:21])[CH3:20].C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C.O>[F:7][C:8]1[C:16]([I:17])=[C:15]([CH3:18])[CH:14]=[CH:13][C:9]=1[C:10]([NH:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([O:22][CH:19]([CH3:21])[CH3:20])[CH:24]=1)=[O:12]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 5732203-(Propan-2-yloxy)anilineHCID 593839002-Fluoro-3-iodo-4-methylbenzoic acid

Product 1

HCID 588297502-fluoro-3-iodo-N-(3-isopropoxyphenyl)-4-methylbenzamideYield 68%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (2 M in DCM) (1832 μl, 3664 μmol) was added to a suspension of 2-fluoro-3-iodo-4-methylbenzoic acid (684 mg, 2443 μmol) in DCM (20 mL) at 0° C. One drop of DMF (cat) was added. The mixture was stirred at RT for 3 h. Solvent was removed under vacuum. DCM (5 mL) was added to the residue and the mixture was added slowly to a mixture of 3-isopropoxybenzenamine (540 μL, 3664 μmol) and triethylamine (681 μL, 4885 μmol) in DCM (10 mL) at 0° C. The mixture was stirred at RT overnight and then water (50 mL) was added. The mixture was extracted with DCM (3×50 mL). The combined organic layers were washed with brine (100 mL) and dried over sodium sulfate. The solvent was removed in vacuo and the residue was purified by preparative TLC eluting with 10% EtOAc/hexane to give the title compound (683 mg, 68%). MS (M+H)+ 414.

Workup

  1. customSolvent was removed under vacuum
  2. additionDCM (5 mL) was added to the residue
  3. stirringThe mixture was stirred at RT overnight
  4. extractionThe mixture was extracted with DCM (3×50 mL)
  5. washThe combined organic layers were washed with brine (100 mL)
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by preparative TLC
  9. washeluting with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-56a74e15bb6f4f67b935a4f709850695
Source dataset
uspto-grants-2011_08
Patent number
US07989461B2

Reaction notes

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