Acetaldehyde → 5-(2-Diethylamino-ethylamino)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one

HRID 1861007Notes

Reaction equation

HRID 1861007 reaction equation
[CH3:1]S(O)(=O)=O.N[CH2:7][CH2:8][NH:9][C:10]1[CH:11]=[C:12]([C:24]2[NH:25][CH:26]=[CH:27][CH:28]=2)[C:13]2[C:14](=[O:23])[NH:15][C:16]3[C:21]=2[C:20]=1[C:19]([F:22])=[CH:18][CH:17]=3.[CH:29](=O)[CH3:30].[C:32]([BH3-])#[N:33].[Na+]>C(Cl)Cl>[CH2:29]([N:33]([CH2:32][CH3:1])[CH2:7][CH2:8][NH:9][C:10]1[CH:11]=[C:12]([C:24]2[NH:25][CH:26]=[CH:27][CH:28]=2)[C:13]2[C:14](=[O:23])[NH:15][C:16]3[C:21]=2[C:20]=1[C:19]([F:22])=[CH:18][CH:17]=3)[CH3:30]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 102727055-(2-amino-ethylamino)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one methanesulfonic acid salt

Product 1

HCID 102702705-(2-Diethylamino-ethylamino)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-(2-amino-ethylamino)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one methanesulfonic acid salt (from Example 11 above) (58.04 mg, 0.14 mmol) in CH2Cl2 (5 mL) were added acetaldehyde (Aldrich, 0.39 mg, 0.39 mmol) and sodium cyanoborohydride (Aldrich, 20.0 mg, 0.32 mmol) at room temperature. The reaction mixture was stirred for 1 hour. The reaction was then quenched with water (5 mL) and extracted with ethyl acetate (3×20 mL). The combined organic extracts were successively washed with water (5 mL) and brine (5 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was triturated with ethyl acetate and hexanes, filtered, and dried to give 5-(2-diethylamino-ethylamino)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one as a brown solid. (Yield 12.0 mg, 23.4%).

Workup

  1. customThe reaction was then quenched with water (5 mL)
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe combined organic extracts were successively washed with water (5 mL) and brine (5 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was triturated with ethyl acetate and hexanes
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-db55663752f642f9bee33de2ba69840f
Source dataset
uspto-grants-2003_03
Patent number
US06531598B1

Reaction notes

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