Diisopropylethylamine → 5-(methyloxy)-1-[(methyloxy)acetyl]-6-nitro-2,3-dihydro-1H-indole

HRID 1014275Notes

Reaction equation

HRID 1014275 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][CH2:7][CH2:6]2.C(N(C(C)C)CC)(C)C.[CH3:24][O:25][CH2:26][C:27](Cl)=[O:28]>C1COCC1.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[N:8]([C:27](=[O:28])[CH2:26][O:25][CH3:24])[CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 594416565-methoxy-6-nitro-2,3-dihydro-1H-indole

Product 1

HCID 594420105-(methyloxy)-1-[(methyloxy)acetyl]-6-nitro-2,3-dihydro-1H-indoleYield 107.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (Intermediate B99, 3.2 g, 13.87 mmol) in THF (100 mL) was treated with diisopropylethylamine (4.83 mL, 27.7 mmol), followed by (methyloxy)acetyl chloride (1.903 mL, 20.81 mmol). The resulting yellow slurry was stirred at rt for 3 days, then diluted with CH2Cl2 (300 mL), washed with water (150 mL), a saturated NaCl solution (150 mL), dried (Na2SO4) and concentrated to obtain 5-(methyloxy)-1-[(methyloxy)acetyl]-6-nitro-2,3-dihydro-1H-indole as an orange solid (3.96 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.24 (t, J=8.42 Hz 2H), 3.36 (s, 3H), 3.89 (s, 3H), 4.07 (t, J=8.42 Hz 2H), 4.19 (s, 2 H), 7.35 (s, 1H), 8.47 (s, 1H); ESIMS (M+H)+=266.87.

Workup

  1. washwashed with water (150 mL)
  2. dry with materiala saturated NaCl solution (150 mL), dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5a295645d2de457aa572aa206602e8d0
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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