Water → HCID 12150689, compound

HRID 2086170Notes

Reaction equation

HRID 2086170 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([CH3:15])[C:11]([O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([C:24](=O)[C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:18]=1)=[C:10]([CH3:33])[CH:9]=2)=[O:5])[CH3:2].C([SiH](CC)CC)C.O.C(OCC)(=O)C>FC(F)(F)C(O)=O.C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([CH3:15])[C:11]([O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[CH:18]=1)=[C:10]([CH3:33])[CH:9]=2)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 12052TriethylsilaneHCID 12150688HCID 12150688, compound

Product 1

HCID 12150689HCID 12150689, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 5-[3-(4-Fluoro-benzoyl)-4-hydroxy-phenoxy]-4,6-dimethyl-1H-indole-2-carboxylic acid ethyl ester (25 mg, 0.056 mmol) in a mixture of trifluoroacetic acid (0.2 mL) and methylene chloride (0.25 mL) at room temperature was added triethylsilane (0.09 mL, 0.56 mmol), and the resulting solution was stirred at room temperature for 18 hours. The reaction solution was poured into water (10 mL) and ethyl acetate (15 mL) was added. The organic phase was washed with saturated aqueous NaHCO3 (2 times 10 mL), brine (10 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative thin layer chromatography (30% ethyl acetate in hexane) to afford the title compound (17.8 mg) as a white solid. 1H NMR (400 MHz, CDCl3) δ8.84 (s, 1H), 7.21 (s, 1H), 7.15-7.09(m, 3H), 6.94 (t, 2H), 6.63 (d, 1H), 6.58 (d, 1H), 6.45-6.42 (dd, 1H), 4.43-4.37 (q, 2H), 3.86 (s, 2H), 2.31 (s, 3H), 2.20 (s, 3H), 1.41 (t, 3H). MS (APCI−) Calc:433.2, Found: 432.1 (M−1).

Workup

  1. additionwas added
  2. washThe organic phase was washed with saturated aqueous NaHCO3 (2 times 10 mL), brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative thin layer chromatography (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b4a75813e2bf417080fb4a5117701905
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

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