Triethylamine → HCID 59799766, compound

HRID 1911882Notes

Reaction equation

HRID 1911882 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].C(N(CC)CC)C.[C:20](Cl)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22]>O1CCCC1>[CH3:22][C:21]([CH3:24])([CH3:23])[C:20]([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]=[N:8]1)=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 215015-NitroindazoleHCID 62493Pivaloyl chloride

Product 1

HCID 59799766HCID 59799766, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 4 L 3-neck round bottom flask fitted with a nitrogen inlet and mechanical stirrer was charged with a solution of 5-nitroindazole (80.0 g, 0.49 mol) in tetrahydrofuran (1 L). The mixture was cooled to 0° C. and triethylamine (85.4 mL, 0.61 mol) was added. To the mixture was added pivaloyl chloride (63.4 mL, 0.52 mol) dropwise over a period of 15 minutes. The reaction was allowed to warm to 20° C. over a period of 2 hours. The reaction was filtered and concentrated to a dark red oil. To the oil was added methylene chloride (60 mL). The resulting slurry was stirred vigorously, giving a white precipitate that was isolated by filtration. The solid was dried in a vacuum oven at 40° C. overnight to afford the title compound (95 g, 79%).

Workup

  1. customA 4 L 3-neck round bottom flask fitted with a nitrogen inlet and mechanical stirrer
  2. temperatureto warm to 20° C. over a period of 2 hours
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated to a dark red oil
  5. additionTo the oil was added methylene chloride (60 mL)
  6. customgiving a white precipitate that
  7. customwas isolated by filtration
  8. customThe solid was dried in a vacuum oven at 40° C. overnight

Sources & evidence

ORD record
ord-cf8c56917d6a4f388a5ff1a91f4d1579
Source dataset
uspto-grants-2013_12
Patent number
US08604205B2

Reaction notes

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