Thionyl Chloride → 5-(3-Bromo-2-methylphenyl)-2-tert-butyl-4H-thieno[3,2-c]pyrrol-6(5H)-one

HRID 1772077Notes

Reaction equation

HRID 1772077 reaction equation
[Br:1][C:2]1[C:3]([CH3:22])=[C:4]([NH:8][CH2:9][C:10]2[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[S:12][C:11]=2[C:19](O)=[O:20])[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH3:22])=[C:4]([N:8]2[C:19](=[O:20])[C:11]3[S:12][C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:14][C:10]=3[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 866979323-((3-Bromo-2-methylphenylamino)methyl)-5-tert-butylthiophene-2-carboxylic Acid

Product 1

HCID 866979335-(3-Bromo-2-methylphenyl)-2-tert-butyl-4H-thieno[3,2-c]pyrrol-6(5H)-oneYield 70.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 250-mL single-necked round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 102e (1.12 g, 2.93 mmol) and anhydrous methylene chloride (50 mL). Thionyl chloride (1.25 g, 10.5 mmol) was added and the reaction was stirred at ambient temperature. After 16 h the reaction was concentrated under reduced pressure. Purification of the resulting residue by column chromatography afforded a 65% yield (757 mg) of 102f as a white solid: mp 185-186° C.; 1H NMR (300 MHz, CDCl3) δ 7.56 (dd, 1H, J=6.6, 1.2 Hz), 7.20 (dd, 1H, J=6.3, 1.5 Hz), 7.11 (t, 1H, 7.8 Hz), 6.87 (s, 1H), 4.56 (s, 2H), 2.33 (s, 3H), 1.45 (s, 9H); MS (ESI+) m/z 364.2 (M+H).

Workup

  1. customA 250-mL single-necked round-bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. concentrationAfter 16 h the reaction was concentrated under reduced pressure
  4. customPurification of the resulting residue by column chromatography

Sources & evidence

ORD record
ord-92e8c2b6988b4eb6b224cd293d1e73c4
Source dataset
uspto-grants-2016_02
Patent number
US09249123B2

Reaction notes

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