Oxalyl chloride → HCID 58488517, compound

HRID 451360Notes

Reaction equation

HRID 451360 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][CH:11]=[C:10]([C:13]([OH:15])=O)[C:9]=2[CH3:16])=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1.C(Cl)(=O)C(Cl)=O.Cl.[CH3:28][S:29]([C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1)(=[O:31])=[O:30].C(N(C(C)C)CC)(C)C>ClCCl.O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][CH:11]=[C:10]([C:13]([NH:36][C:35]3[CH:34]=[CH:33][C:32]([S:29]([CH3:28])(=[O:31])=[O:30])=[CH:38][CH:37]=3)=[O:15])[C:9]=2[CH3:16])=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 27351804-(Methylsulfonyl)aniline hydrochlorideHCID 584885215-[4-fluoro-2-(trifluoromethyl)phenyl]-4-methyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 58488517HCID 58488517, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-[4-fluoro-2-(trifluoromethyl)phenyl]-4-methyl-1H-pyrrole-3-carboxylic acid (7.7 g, 27 mmol) in dichloromethane (60 ml) was added oxalyl chloride (5.1 ml, 59 mmol). The mixture was stirred at room temperature for 2.0 h, after which time the solvent was removed on a rotary evaporator. To this brown residue was added 4-(methanesulfonyl)aniline hydrochloride (5.8 g, 28 mmol), tetrahydrofuran (THF) (80 ml) and diisopropylethylamine (DIEA) (14 ml, 80 mmol). The solution was stirred at room temperature for 2.0 h. The reaction mixture was concentrated and to the residue was added 2N HCl (80 ml) and water (80 ml) and resulting suspension was stirred for 30 min. The solid was filtered and washed with water and diisopropyl ether (IPE) to give the title compound as a white solid (11 g, 90%).

Workup

  1. customafter which time the solvent was removed on a rotary evaporator
  2. stirringThe solution was stirred at room temperature for 2.0 h
  3. concentrationThe reaction mixture was concentrated and to the residue
  4. additionwas added 2N HCl (80 ml) and water (80 ml)
  5. customresulting suspension
  6. stirringwas stirred for 30 min
  7. filtrationThe solid was filtered
  8. washwashed with water and diisopropyl ether (IPE)

Sources & evidence

ORD record
ord-2cc8a95f1dc442f3a42d2ae7faaa050e
Source dataset
uspto-grants-2013_07
Patent number
US08487117B2

Reaction notes

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