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Hydrochloric Acid → 2-(1-Benzenesulfonyl-1H-pyrrol-3-yl)-1-(2,3-difluoro-phenyl)-ethanone

HRID 2249513
Notes
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Reaction equation

HRID 2249513 reaction equation
[C:1]1([S:7]([N:10]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]N([Si](C)(C)C)[Si](C)(C)C.COC(=O)[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:33]=1[F:39].Cl>C1COCC1>[C:1]1([S:7]([N:10]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:33]=3[F:39])=[O:18])=[CH:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2782927Methyl 2,3-difluorobenzoateHCID 13157056(1-Benzenesulfonyl-1H-pyrrol-3-yl)-acetic acidHCID 178418261HCID 178418261, compound

Product 1

HCID 692886012-(1-Benzenesulfonyl-1H-pyrrol-3-yl)-1-(2,3-difluoro-phenyl)-ethanoneYield 62.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (1-benzenesulfonyl-1H-pyrrol-3-yl)-acetic acid (1.3 g, 4.90 mmol) in THF was added LiN(TMS)2 (12 mL, 1.0M in THF, 12 mmol) at −78° C. The resulting solution was stirred at this temperature for 1 hour and 0° C. for 1 hour and then was cooled to −78° C. again. To this solution was added 2,3-difluoro-benzoic acid methyl ester (1.1 g, 6.40 mmol) and the reaction was stirred at room temperature for 14 hours. The solution was poured into 2N HCl and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and evaporated. The crude product was purified by flash column eluting with 20% of EtOAc in hexanes to afford the title compound as a yellow oil (1.1 g, 58%). 1H NMR (500 MHz, CDCl3) δ7.77 (d, 2H), 7.50 (m, 2H), 7.42 (t, 2H), 7.28 (m, 1H), 7.05 (m, 3H), 6.18 (m, 1H), 3.98 (s, 2H) ppm. MS (ES+): m/e=362.1 (M+H); LC/Method A/3.98 min.

Workup

  1. temperaturewas cooled to −78° C. again
  2. stirringthe reaction was stirred at room temperature for 14 hours
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash column
  8. washeluting with 20% of EtOAc in hexanes

Sources & evidence

ORD record
ord-d14bddca6d8e4c64a4c4f8930f0d7837
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07314885B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes