HCID 57443977, compound → HCID 57443978, compound

HRID 1172860Notes

Reaction equation

HRID 1172860 reaction equation
[N:1]([CH:4]([C:6]1[CH:19]=[CH:18][C:9]2[CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:12][C:8]=2[CH:7]=1)[CH3:5])=[N+]=[N-]>CCOC(C)=O.[Pd]>[NH2:1][CH:4]([C:6]1[CH:19]=[CH:18][C:9]2[CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:12][C:8]=2[CH:7]=1)[CH3:5]

Participants

4

Reactant 1

HCID 57443977HCID 57443977, compound

Product 1

HCID 57443978HCID 57443978, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 6-(1-azidoethyl)-1-benzothiophene-2-carboxylate (1.7 g, 6.17 mmol) in EtOAc (50 mL) was added 10% Pd/C (170 mg), and the resultant slurry was hydrogenated under 1 atm of H2 for 4 h at RT. The reaction mixture was filtered via Celite and the filtrate was concentrated and dried to give the desired product. 1H NMR (CDCl3, 600 MHz) δ 8.01 (d, J=0.9 Hz, 1H), 7.84 (m, 1H), 7.81 (d, J=8.2 Hz, 1H), 7.38 (dd, J=8.2, 0.9 Hz, 1H), 4.39 (q, J=7.3 Hz, 2H), 4.25 (q, J=6.8 Hz, 1H), 1.44 (d, J=6.8 Hz, 3H), 1.40 (t, J=7.3 Hz, 3H). MS: cal'd 250 (MH+), exp 250 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered via Celite
  2. concentrationthe filtrate was concentrated
  3. customdried

Sources & evidence

ORD record
ord-09583ffee5aa4bbf94a0e9f911d29d57
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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