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Trifluoroacetic acid → ethyl [4-bromo-3-(6-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

HRID 645053
Notes
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Reaction equation

HRID 645053 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([Br:15])[CH:11]=[CH:12][CH:13]=2)[C:8](O)([C:16]2[C:17]([OH:27])=[CH:18][C:19]3[O:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20]=3[CH:26]=2)[C:7]1=[O:29])[CH3:2].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([Br:15])[CH:11]=[CH:12][CH:13]=2)[CH:8]([C:16]2[C:17]([OH:27])=[CH:18][C:19]3[O:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20]=3[CH:26]=2)[C:7]1=[O:29])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58872452ethyl [4-bromo-3-hydroxy-3-(6-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

Product 1

HCID 58872473ethyl [4-bromo-3-(6-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetateYield 81%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Conditions

Temperature
35 °C

Procedure

A mixture of ethyl[4-bromo-3-hydroxy-3-(6-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate (1.32 g, 2.80 mmol), triethylsilane (2.00 mL, 12.2 mmol) and trifluoroacetic acid (0.94 mL, 12.2 mmol) in dichloromethane (50.0 mL) was stirred at 35° C. for 3 hours. The mixture was diluted with dichloromethane (100 mL), washed with water, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography (ethyl acetate/hexane, 1/3) to give the title compound (1.04 g, 81%): 1H NMR (300 MHz, CDCl3) δ 7.32-7.15 (m, 2H), 6.74 (d, 1H), 6.50-6.36 (br, 2H), 5.04 (s, 1H), 4.51-4.34 (m, 2H), 4.25-4.14 (m, 2H), 2.92-2.69 (m, 2H), 1.43 (s, 3H), 1.37 (s, 3H), 1.23 (t, 3H); MS (ES+) m/z 460.5 (M+1), 462.5 (M+1).

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-65c0d85a33d042739ae4432914e93ff1
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07700641B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes