HCID 86612409, compound → 5-Amino-3-(4-tert-butyl-phenyl)-4-cyano-thiophene-2-carboxylic acid methyl ester

HRID 1990082Notes

Reaction equation

HRID 1990082 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([N:22]=[N+]=[N-])=[C:8]([C:20]#[N:21])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1C(C)(C)C)=[O:4]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([NH2:22])=[C:8]([C:20]#[N:21])[C:9]=1[C:10]1[CH:11]=[CH:12][C:13]([C:8]([CH3:20])([CH3:9])[CH3:7])=[CH:14][CH:15]=1)=[O:4]

Participants

3

Reactant 1

HCID 86612409HCID 86612409, compound

Product 1

HCID 685220375-Amino-3-(4-tert-butyl-phenyl)-4-cyano-thiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Combine 5-azido-3-(tert-butyl-phenyl)-4-cyano-thiophene-2-carboxylic acid methyl ester (0.309 mmol) and THF at room temperature and add a fresh THF solution of 0.1M SmI (0.93 mmol). Stir the reaction for 15 minutes and quench with 2M sodium carbonate solution until pH was greater than 9.0. Dilute the reaction with ethyl acetate and wash successively with 2M sodium carbonate, water, and brine. Separate the organics, dry over sodium sulfate, filter, and concentrate to give the title compound as a dark solid: 1H NMR (400 MHz, CDCl3) δ 7.46-7.36 (m, 4H), 5.23 (s, 2H), 3.71 (s, 3H), 1.36 (s, 9H), MS found (M+1) 315.1.

Workup

  1. customthe reaction for 15 minutes
  2. customquench with 2M sodium carbonate solution until pH was greater than 9.0
  3. additionDilute
  4. customthe reaction with ethyl acetate
  5. washwash successively with 2M sodium carbonate, water, and brine
  6. customSeparate the organics,
  7. dry with materialdry over sodium sulfate
  8. filtrationfilter
  9. concentrationconcentrate

Sources & evidence

ORD record
ord-814546e827404e1aa7e3e55eee3dda51
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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