Dichloromethane → HCID 57217102, compound

HRID 1418687Notes

Reaction equation

HRID 1418687 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]1[CH2:19][N:18]3[C:13](=[CH:14][C:15]([C:22](=[O:25])[CH2:23][CH3:24])=[C:16]([CH3:21])[C:17]3=[O:20])[C:7]1=[N:8]2.C(Cl)Cl.C1COCC1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]1[CH2:19][N:18]3[C:13](=[CH:14][C:15]([CH:22]([OH:25])[CH2:23][CH3:24])=[C:16]([CH3:21])[C:17]3=[O:20])[C:7]1=[N:8]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 10314820HCID 10314820, compound

Product 1

HCID 57217102HCID 57217102, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-methoxy-8-methyl-7-(1-oxopropyl)indolizino[1,2-b]quinolin-9(11H)-one (5.0 mg, 15 μmol) in a mixture of MeOH (0.2 mL), CH2Cl2 (0.6 mL) and THF (0.2 mL) was treated with a single portion of sodium borohydride (4.0 mg, 110 ,μmol). After stirring at room temperature for 1.5 h, the reaction mixture was concentrated under reduced pressure. The residue was treated with 10% aqueous NH4Cl (350 μL) and allowed to stand at 4° C. overnight. The solid which formed was collected by filtration, washed sparingly with H2O and dried to afford the title compound. 1H NMR (CDCl3 /MeOH-d4) d 8.77 (s, 1H), 7.69 (m, 2H), 7.59 (s, 1H), 6.92 (dd, J=6.8, 1.7 Hz, 1H), 5.23 (br s, 2H), 4.89 (m, 1H), 4.05 (s, 3H), 2.24 (s, 3H), 1.79 (m, 2H), 1.03 (t, J=7.4 Hz, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was treated with 10% aqueous NH4Cl (350 μL)
  3. waitto stand at 4° C. overnight
  4. customThe solid which formed
  5. filtrationwas collected by filtration
  6. washwashed sparingly with H2O
  7. customdried

Sources & evidence

ORD record
ord-483cea06f134451d86d0c3bac69f331a
Source dataset
uspto-grants-1999_03
Patent number
US05883255

Reaction notes

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