Water → HCID 9867927, compound

HRID 428652Notes

Reaction equation

HRID 428652 reaction equation
I[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:12]/[C:13]1[NH:14][CH:15]=[CH:16][CH:17]=1)/[C:5](=[O:11])[NH:6]2.[CH2:18]([N:21]1[C:34](=[O:35])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]1=2)[C:19]#[CH:20].O>O1CCCC1.C(N(CC)CC)C.[Cu]I.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:11]=[C:5]1[NH:6][C:7]2[C:3](/[C:4]/1=[CH:12]/[C:13]1[NH:14][CH:15]=[CH:16][CH:17]=1)=[C:2]([C:20]#[C:19][CH2:18][N:21]1[C:34](=[O:35])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]1=3)[CH:10]=[CH:9][CH:8]=2

Participants

8

Reactant 3

HCID 962WaterHCID 14894694HCID 14894694, compoundHCID 15548052(Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-indol-2-one

Product 1

HCID 9867927HCID 9867927, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A solution of (Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (from Example 71, infra) (50 mg, 0.15 mmol), and 5-(2-propynyl)-6(5H)-phenanthridinone (45 mg, 0.19 mmol) (prepared according to Walser et al., J. Med. Chem. 34(3), 1209-1221 (1991)) in 1 mL tetrahydrofuran and 1 mL triethylamine was degassed by bubbling argon through the solution for 10 minutes. At this time, copper (I) iodide (11 mg, 0.06 mmol) and tetrakis(triphenylphosphine) palladium(0) (3 mg, 0.03 mmol) were added, and the reaction was stirred at room temperature for 72 hours. Water (10 mL) was then added and the precipitate was filtered off and dried. The product was purified via flash column chromatography (SiO2, 230-400 mesh) with ethyl acetate/hexane, to yield a yellow powder which was recrystallized from ethyl acetate/hexane, to give (Z)-5-[3-[2,3-dihydro-2-oxo-3-(1H-pyrrol-2-ylmethylene)-1H-indol-4-yl]-2-propynyl]-6(5H)-phenanthridinone. (Yield 25 mg, 38%).

Workup

  1. customby bubbling argon through the solution for 10 minutes
  2. filtrationthe precipitate was filtered off
  3. customdried
  4. customThe product was purified via flash column chromatography (SiO2, 230-400 mesh) with ethyl acetate/hexane
  5. customto yield a yellow powder which
  6. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1479dba332be46fe848067d6b4cda794
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

Loading…