Benzoyl chloride → HCID 69037395, compound

HRID 1865168Notes

Reaction equation

HRID 1865168 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2)([O-:3])=[O:2].[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCN(CC)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:18]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:7]=[C:8]1[C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 280312Ethyl 5-nitro-1H-indole-2-carboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 69037395HCID 69037395, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Ethyl 5-nitroindole-2-carboxylate (3.1) (1.5 g, 6.41 mmol) in CH2Cl2 (30 ml) was treated with benzoyl chloride (1.19 ml, 10.26 mmol), Et3N (891 μl, 6.41 mmol) and DMAP (783 mg, 6.41 mmol). The mixture was stirred for 16 h. 10% NaHCO3 (10 ml) and CH2Cl2 (10 ml) were added and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (3×5 mL). The combined organic layers were washed with H2O (10 ml), 5% HCl (10 ml) and H2O (10 ml). The solution was dried (MgSO4) and concentrated. The 10 residue was crystalised from EtOAc/Hex 1:9 to afford 1.85 g (87%) of 3.2 as a yellow powder: 1H NMR (250 MHz, CDCl3) δ ppm 8.66 (d, 1H), 8.25 (d, 1H), 7.80 (d,1H), 7.6-7.72 (m, 3H), 7.48 (m, 3H), 4.00 (q, 2H), 1.10 (t, 3H). FABMS (NBA/NaI) m/z 339 (M+H+ expected 339)

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted with CH2Cl2 (3×5 mL)
  3. washThe combined organic layers were washed with H2O (10 ml), 5% HCl (10 ml) and H2O (10 ml)
  4. dry with materialThe solution was dried (MgSO4)
  5. concentrationconcentrated
  6. customThe 10 residue was crystalised from EtOAc/Hex 1:9

Sources & evidence

ORD record
ord-661be6d0132d4390a5536ab5da653f90
Source dataset
uspto-grants-2009_12
Patent number
US07626026B2

Reaction notes

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