Triethylamine → HCID 59440245, compound

HRID 2405729Notes

Reaction equation

HRID 2405729 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH:9]([C:13]([O:15][CH3:16])=[O:14])[NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:17]([O:24][C:25]1[C:33]([O:34][CH3:35])=[CH:32][C:28]([C:29](Cl)=[O:30])=[C:27]([N+:36]([O-:38])=[O:37])[CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N1C2C(=CC=CC=2)CC1.C(N(CC)CC)C>O1CCCC1>[CH2:17]([O:24][C:25]1[C:33]([O:34][CH3:35])=[CH:32][C:28]([C:29]([N:10]2[C:11]3[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=3)[CH2:8][CH:9]2[C:13]([O:15][CH3:16])=[O:14])=[O:30])=[C:27]([N+:36]([O-:38])=[O:37])[CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10328IndolineHCID 12032223methyl 6-nitroindoline-2-carboxylateHCID 125064114-(Benzyloxy)-5-methoxy-2-nitrobenzoyl chloride2×

Product 1

HCID 59440245HCID 59440245, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl 6-nitroindoline-2-carboxylate (258a) (0.233 g, 1.048 mmol) was dissolved in anhydrous tetrahydrofuran (4 ml) in a separate flask and cooled to 0° C. an ice bath. In another flask 4-(benzyloxy)-5-methoxy-2-nitrobenzoyl chloride (4) (0.371 g, 1.153 mmol) was dissolved in anhydrous tetrahydrofuran (4 ml) and cooled to 0° C. in an ice bath. To the flask containing the indoline was added triethylamine (0.438 ml, 3.15 mmol) via syringe and the acetyl chloride 4 was added quickly to the reaction mixture via cannula at 0° C. The reaction was stirred for 90 minutes at 0° C. and then at room temperature for an additional 1 hour. The reaction was then quenched with 5% HCl and extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography using 30% Acetone in hexane to give methyl 1-(4-(benzyloxy)-5-methoxy-2-nitrobenzoyl)-6-nitroindoline-2-carboxylate (258b) (0.220 g, 0.434 mmol, 41.4% yield) as a yellowish foam. 1H NMR (400 Hz, CDCl3): δ 3.30 (m, 1H), 3.60 (s, 3H), 3.69 (m, 1H), 3.86 (s, 3H), 4.64 (dd, 1H, J=2.4 Hz, 10.8), 5.23 (s, 2H), 7.31 (m, 1H), 7.46 (m, 6H), 7.99 (dd, 1H, J=2.0, 8.0 Hz), 9.04 (d, 1H, J=2.0 Hz). MS (m/z): found 530.1 ([M]++Na).

Workup

  1. temperaturecooled to 0° C. in an ice bath
  2. waitat room temperature for an additional 1 hour
  3. customThe reaction was then quenched with 5% HCl
  4. extractionextracted with ethyl acetate (3×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5e4d8f6008e1482b966249a40b444525
Source dataset
uspto-grants-2014_08
Patent number
US08809320B2

Reaction notes

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