Water → HCID 67290752, compound

HRID 511845Notes

Reaction equation

HRID 511845 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([S:13]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:10]=[C:9]2[CH:23]=O.[OH2:25].[CH2:26]1[CH2:30][O:29][CH2:28][CH2:27]1>>[F:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([S:13]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:10]=[C:9]2/[CH:23]=[CH:27]/[C:28]([O:29][CH2:30][CH3:26])=[O:25]

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 11594861HCID 11594861, compound

Product 1

HCID 67290752HCID 67290752, compoundYield 65%

Procedure

To a suspension of sodium hydride (ca 60%, 240 mg, 6.3 mmol) in THF (10 mL) was added dropwise a solution of triethyl phosphonoacetate (1.33 g, 5.9 mmol) in THF (5 mL) at 0° C. After stirring at room temperature for 0.5 hour, a solution of 7-fluoro-1-tos yl-1H-indole-3-carbaldehyde (J. Med. Chem., 48 (19), 6023-6034 (2005)) (1.10 g, 3.48 mmol) in THF (5 mL) was added to the mixture at 0° C. The resulting mixture was stirred at 0° C. for 0.5 hour and at room temperature for 19 hours. The mixture was poured into water, extracted with dichloromethane, dried over sodium sulfate, filtered and concentrated in vacuo. The residual solid was washed with ethyl acetate to give 864 mg (65% yield) of the title compound as a white solid:

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for 0.5 hour and at room temperature for 19 hours
  2. extractionextracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe residual solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-93fd643f42784454a24a31d82b001b7d
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

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