Ethyl bromoacetate → HCID 19711282, compound

HRID 233086Notes

Reaction equation

HRID 233086 reaction equation
[CH:1]1[C:6]2[CH2:7][C:8]3[C:20]4[NH:19][C:18]5[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=5)[C:12]=4[C:11]4[C:21](=[O:24])[NH:22][CH2:23][C:10]=4[C:9]=3[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:28][C:29](OCC)=[O:30].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CN(C=O)C.C1COCC1>[OH:30][CH2:29][CH2:28][CH:7]1[C:8]2[C:20]3[NH:19][C:18]4[C:13]([C:12]=3[C:11]3[C:21](=[O:24])[NH:22][CH2:23][C:10]=3[C:9]=2[C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:6]1=2)=[CH:14][CH:15]=[CH:16][CH:17]=4

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 11809063HCID 11809063, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19711282HCID 19711282, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

5H,6H,12H,13H-indeno[2,3-a]pyrrolo[3,4-c]carbazole-7(7H)one (Compound I-2) (200 mg, 0.65 mmol) was added to a stirred solution of NaH (25 mg of 60% oil dispersion, 0.65 mmol) in dry DMF (10 mL) under a nitrogen atmosphere. The dark mixture was stirred at ambient temperature for 1 hour. Ethyl bromoacetate (120 mg, 0.08 mL, 0.72) was added dropwise and the mixture was stirred 12 hours. The resulting yellow solution was concentrated at reduced pressure to give a crude yellow solid. The product was dissolved in dry THF (10 mL) and lithium aluminium hydride (1 mL of 1M solution in ether) was added dropwise. The solution was stirred 6 hours at room temperature, then the reaction was quenched by the addition of H2O (1 mL). The mixture was filtered and concentrated at reduced pressure. THF was added to the residue and the product was collected to give 30 mg (17%) of Compound I-29 as a white solid. The melting point was greater than 300° C. The following NMR data were obtained: 1H NMR (DMSO-d6, 300 MHz): δ 3.8-3.9 (b, 2H), 4.55 (s, 2H), 4.77 (t, 2H), 4.9 (s, 2H), 5.0 (b, 1H, D2O exchange), 7.3-7.45 (m, 3H), 7.5-7.57 (t, 1H), 7.67 (d, 1H, J=6 Hz), 7.5 (d, 1H, J=6 Hz), 8.0 (d, 1H, J=6 Hz); 8.57 (s, 1H), 9.5 (d, 1H, J=7 Hz). MS(FAB): m/e 355 (M+1)+.

Workup

  1. stirringthe mixture was stirred 12 hours
  2. concentrationThe resulting yellow solution was concentrated at reduced pressure
  3. customto give a crude yellow solid
  4. stirringThe solution was stirred 6 hours at room temperature
  5. customthe reaction was quenched by the addition of H2O (1 mL)
  6. filtrationThe mixture was filtered
  7. concentrationconcentrated at reduced pressure
  8. additionTHF was added to the residue
  9. customthe product was collected

Sources & evidence

ORD record
ord-f1244de9b6384e4fbaa66cfdcc1a8cea
Source dataset
uspto-grants-1997_01
Patent number
US05591855

Reaction notes

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