1H-Indole-3-propanoic acid → 3-(1H-indol-3-yl)-1-(pyrrolidin-1-yl)propan-1-one

HRID 74521

Reaction equation

HRID 74521 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:2]1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:14])=[CH:2]1

Participants

6

Reactant 4

HCID 37441H-Indole-3-propanoic acidHCID 8471TriethylamineHCID 31268PyrrolidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 48067833-(1H-indol-3-yl)-1-(pyrrolidin-1-yl)propan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

681 mg (3.60 mmol) 3-(1H-indol-3-yl)-propionic acid, 0.3 mL (3.60 mmol) pyrrolidine, 1.13 g (3.50 mmol) TBTU and 0.98 mL (7.00 mmol) triethylamine in 5.0 mL DMF were stirred overnight at RT. The mixture was purified by preparative HPLC. The product fractions were combined and evaporated down i. vac.

Workup

  1. customThe mixture was purified by preparative HPLC
  2. customevaporated down i

Sources & evidence

ORD record
ord-1df2c89023ab44e3bf397e899e470f39
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

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