Acetone → 1H-Indolamine

HRID 966510Notes

Reaction equation

HRID 966510 reaction equation
Cl.C(OC([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18](OC3CCNC3)[CH:19]=2)[NH:14][C:13]=1C)=O)C1C=CC=CC=1.CC(C)=O.C([BH3-])#[N:33].[Na+]>CO>[NH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[C:13]1[NH2:33]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 1317251792-Methyl-5-(pyrrolidin-3-yloxy)-1h-indole-3-carboxylic acid benzyl ester, hydrochloride

Product 1

HCID 1220741H-IndolamineYield 189.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude 2-methyl-5-(pyrrolidin-3-yloxy)-1H-indole-3-carboxylic acid benzyl ester, hydrochloride (0.040 g, 0.100 mmol, 1 eq, Example 47, Step A) was suspended in methanol (5 mL). Acetone (0.100 mL) was added followed by the addition of sodium cyanoborohydride (0.013 g, 0.2 mmol, 2.0 eq). The reaction mixture was kept at pH 6 and stirred at room temperature. After 24 hours, the reaction was quenched with aqueous sodium bicarbonate, extracted several times with CH2Cl2. The combined organic layers were dried over sodium sulfate, loaded on silica gel and chromatographed (ethyl acetate/methanol/triethylamine 87/10/3. 0.025 g (64% yield) of the indole-amine was obtained as a brown semisolid, and converted to the corresponding HCl salt: LC/MS (ESI+) 393 (M+1), Anal. (C24H28N2O3.HCl) C, H, N.

Workup

  1. customthe reaction was quenched with aqueous sodium bicarbonate
  2. extractionextracted several times with CH2Cl2
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customchromatographed (ethyl acetate/methanol/triethylamine 87/10/3

Sources & evidence

ORD record
ord-889e5554a7ae464782ce5198c27ed3c4
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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