HCID 21460773, compound → HCID 21460740, compound

HRID 2396337Notes

Reaction equation

HRID 2396337 reaction equation
[C:1]([CH2:6][NH:7][C:8]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11])([O:3][CH2:4][CH3:5])=[O:2].CC(C)([O-])C.[K+]>O1CCCC1.C(OCC)(=O)C>[NH2:11][C:10]1[C:9]2[C:8](=[CH:15][C:14]([C:16]([F:18])([F:17])[F:19])=[CH:13][CH:12]=2)[NH:7][C:6]=1[C:1]([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 21460773HCID 21460773, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21460740HCID 21460740, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 2-(Carbethoxy)methylamino-4-trifluoromethylbenzonitrile (2.34 g, 8.6 mmol) in tetrahydrofuran (40 mL) and add dropwise with stirring to a solution of potassium tert-butoxide (9.46 mL of a 1M tetrahydrofuran solution) under a nitrogen atmosphere at 0° C. The reaction was allowed to warm to room temperature. After 3 hour, dilute with ethyl acetate, rinse with water, saturated sodium chloride, dry magnesium sulfate, filter and concentrate in vacuo. Purify the residue by flash chromatography to yield the 3-amino-2-carbethoxy-6trifluoromethylindole (1.22 g, 52%); mp 204°-210° C.

Workup

  1. additionadd dropwise
  2. washrinse with water, saturated sodium chloride, dry magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify the residue by flash chromatography

Sources & evidence

ORD record
ord-91471d728a2740fe8a089ebf186f6e2c
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

Loading…