O,O-Dipyridin-2-yl carbonothioate → 1-t-Butoxycarbonyl-2,3-dihydro-6-isothiocyanato-7-methylindole

HRID 1275651Notes

Reaction equation

HRID 1275651 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:4][CH:3]=1.C1C=C(O[C:26](OC2N=CC=CC=2)=[S:27])N=CC=1>C(Cl)Cl>[C:15]([O:14][C:12]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([N:1]=[C:26]=[S:27])[C:10]=2[CH3:11])[CH2:6][CH2:7]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 158963716-Amino-1-t-butoxycarbonyl-2,3-dihydro-7-methylindole

Product 1

HCID 158963721-t-Butoxycarbonyl-2,3-dihydro-6-isothiocyanato-7-methylindoleYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-Amino-1-t-butoxycarbonyl-2,3-dihydro-7-methylindole (0.5 g, 2.13 mmol) is dissolved in methylene chloride (10 mL). To this solution is added N,N-dimethylaminopyridine (0.052 g, 0.42 mmol) and di-2-pyridyl thionocarbonate (0.496 g, 2.13 mmol). The solution is allowed to stir for 20 minutes. The solution is diluted with methylene chloride and washed first with four 75-mL portions of aqueous citric acid solution followed by three 100-mL portions of aqueous potassium carbonate. The organic extracts are dried over anhydrous potassium carbonate, filtered and the solvent is removed by rotary evaporation to yield 0.59 g of crude 1-t-butoxycarbonyl-2,3-dihydro-6-isothiocyanato-7-methylindole as an orange, oily solid. The crude product is taken on to the next reaction without further purification.

Workup

  1. washwashed first with four 75-mL portions of aqueous citric acid solution
  2. dry with materialThe organic extracts are dried over anhydrous potassium carbonate
  3. filtrationfiltered
  4. customthe solvent is removed by rotary evaporation

Sources & evidence

ORD record
ord-536f35938d5e44fc9b71fcb4fb929573
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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