Trifluoroacetic acid → Ethyl 6-amino-5-bromo-2-(cyclopent-1-en-1-yl)benzofuran-3-carboxylate

HRID 595580Notes

Reaction equation

HRID 595580 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9]1[C:28]([Br:29])=[CH:27][C:12]2[C:13]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:14]([C:16]3(O)[CH2:20][CH2:19][CH2:18][CH2:17]3)[O:15][C:11]=2[CH:10]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:8][C:9]1[C:28]([Br:29])=[CH:27][C:12]2[C:13]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:14]([C:16]3[CH2:20][CH2:19][CH2:18][CH:17]=3)[O:15][C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 90332481Ethyl 6-amino-5-bromo-2-(1-hydroxycyclopentyl)benzofuran-3-carboxylate

Product 1

HCID 90332430Ethyl 6-amino-5-bromo-2-(cyclopent-1-en-1-yl)benzofuran-3-carboxylateYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

TFA (1.5 mL) was added into a solution of ethyl 6-amino-5-bromo-2-(1-hydroxycyclopentyl)benzofuran-3-carboxylate (2.9 g, 7.89 mmol) in DCM (30 mL), then the mixture was stirred at 25° C. for 12 hours. The reaction mixture was poured into ice water, adjusted to pH=7 with NaHCO3 (a.q.), then the residue was extracted with DCM (50 mL*3), dried over Na2SO4, and concentrated to give the product of ethyl 6-amino-5-bromo-2-(cyclopent-1-en-1-yl)benzofuran-3-carboxylate (2.6 g, yield: 94%). 1H-NMR (CDCl3, 400 MHz) δ 7.99 (s, 1H), 7.11 (t, J=7.2 Hz, 1H), 6.83 (s, 1H), 4.43 (q, J=7.2 Hz, 2H), 2.86˜2.91 (m, 2H), 2.59˜2.63 (m, 2H), 2.01 (t, J=8.0 Hz, 2H), 1.46 (t, J=3.2 Hz, 3H). MS (M+H)+: 350/352.

Workup

  1. extractionthe residue was extracted with DCM (50 mL*3)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8e25416788184da89266ca36f4972415
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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