Triethylamine → HCID 67570742, compound

HRID 363319Notes

Reaction equation

HRID 363319 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[CH:15]2.C(N(CC)CC)C.[OH-].[Na+]>O1CCCC1.O>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:17]2[C:18]3[C:14](=[CH:13][C:12]([NH2:11])=[CH:20][CH:19]=3)[CH:15]=[CH:16]2)=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 678794-Fluorobenzoyl chlorideHCID 788675-Aminoindole

Product 1

HCID 67570742HCID 67570742, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 4-fluorobenzoyl chloride (5.2 g, 33 mmol) in 30 ml of tetrahydrofuran was added dropwise to a solution of the 5-amino-1H-indole (3.96 g, 30.0 mmol) and triethylamine (4.04 g, 40 mmol) at room temperature. The reaction was stirred for 18 hours and then poured into water. The mixture was made basic with sodium hydroxide solution then extracted with methylene chloride. The extract was dried (sodium sulfate) and concentrated. The residue was recrystallized from ethyl acetate/hexanes to give 6.37 g of product. (84%).

Workup

  1. extractionthen extracted with methylene chloride
  2. dry with materialThe extract was dried (sodium sulfate)
  3. concentrationconcentrated
  4. customThe residue was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-096480a450584a5c98b14626900079a7
Source dataset
uspto-grants-1999_02
Patent number
US05874427

Reaction notes

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