Diethylamine → HCID 67315155, compound

HRID 1011360Notes

Reaction equation

HRID 1011360 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:12]1[C:20]2[C:15](=[N:16][C:17]([CH:21]=[CH2:22])=[CH:18][CH:19]=2)[CH2:14][O:13]1.[CH2:23]([NH:25][CH2:26][CH3:27])[CH3:24]>O1CCOCC1.C(N(CC)CC)C>[CH2:23]([N:25]([CH2:26][CH3:27])[CH2:22][CH2:21][C:17]1[N:16]=[C:15]2[CH2:14][O:13][C:12](=[C:5]3[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=4)[NH:7][C:6]3=[O:11])[C:20]2=[CH:19][CH:18]=1)[CH3:24]

Participants

5

Reactant 2

HCID 8021Diethylamine2×HCID 67314553HCID 67314553, compound

Product 1

HCID 67315155HCID 67315155, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 5-fluoro-3-(2-vinyl-7H-furo[3,4-b]pyridin-5-ylidene)-1,3-dihydro-indol-2-one (60 mg, 0.20 mmol) and diethylamine (250 mg, 3.42 mmol) are reacted in a sealed tube at 100° C. for 2 h. The reaction vessel is cooled and additional diethylamine (250 mg, 3.42 mmol) in dioxane (10 mL) is added. The reaction vessel is sealed and heated at 100° C. overnight. The reaction mixture is cooled and treated with triethylamine (15 drops). The reaction mixture is loaded onto silica gel and purified by chromatography (silica gel, MeOH-Chloroform). The product containing fractions are concentrated to provide the title compound (13 mg, 18%) as a yellow solid.

Workup

  1. temperatureThe reaction vessel is cooled
  2. customThe reaction vessel is sealed
  3. temperatureThe reaction mixture is cooled
  4. custompurified by chromatography (silica gel, MeOH-Chloroform)
  5. additionThe product containing fractions
  6. concentrationare concentrated

Sources & evidence

ORD record
ord-ec2319ed42b94ccbaac470d2e9a2b734
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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