2-Methyl-3-furanthiol → 4-(2-Methyl-furan-3-ylsulfanyl)-5-nitro-thiophene-2-carboxylic acid methyl ester

HRID 723072

Reaction equation

HRID 723072 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8](Br)[CH:9]=1)=[O:4].[CH3:14][C:15]1[O:16][CH:17]=[CH:18][C:19]=1[SH:20]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8]([S:20][C:19]2[CH:18]=[CH:17][O:16][C:15]=2[CH3:14])[CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 342862-Methyl-3-furanthiolHCID 13291027Methyl 4-bromo-5-nitrothiophene-2-carboxylate

Product 1

HCID 695867094-(2-Methyl-furan-3-ylsulfanyl)-5-nitro-thiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Bromo-5-nitro-thiophene-2-carboxylic acid methyl ester ((Example 114, step c) 532 mg, 2 mmol), 2-methyl-furan-3-thiol (600 mg, 5.26 mmol), and DMAP-polystyrene resin (2 g, 2.86 mmol) were stirred in THF (10 mL) for 12 h at rt. The resin was filtered and washed with several portions of DCM (100 mL total volume). The filtrate was concentrated in vacuo and the yellow residue (480 mg, 80%) was used without further purification. 1H-NMR (CDCl3): δ 7.46 (d, 1H, J=1.9 Hz), 7.05 (s, 1H), 6.43 (d, 1H, J=1.9 Hz), 3.90 (s, 3H), 2.38 (s, 3H).

Workup

  1. filtrationThe resin was filtered
  2. washwashed with several portions of DCM (100 mL total volume)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe yellow residue (480 mg, 80%) was used without further purification

Sources & evidence

ORD record
ord-d22bd471740c4942b41b1c5b6c0f7975
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Linked notes

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