Tributylphosphine → Ethyl 5-fluoro-1-[2-(pyridin-3-yl)ethyl]-1H-indole-2-carboxylate

HRID 1028035Notes

Reaction equation

HRID 1028035 reaction equation
N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[F:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23]2.[N:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][CH2:41]O)[CH:35]=1.C(P(CCCC)CCCC)CCC>O1CCCC1>[F:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([CH2:41][CH2:40][C:36]1[CH:35]=[N:34][CH:39]=[CH:38][CH:37]=1)[C:24]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23]2

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 805153-PyridineethanolHCID 2727899ethyl 5-fluoro-1H-indole-2-carboxylate

Product 1

HCID 15978980Ethyl 5-fluoro-1-[2-(pyridin-3-yl)ethyl]-1H-indole-2-carboxylateYield 41.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.365 g (1.44 mmol) of 1,1′-(azodicarbonyl)dipiperidine in 10 ml of tetrahydrofuran is added dropwise to a solution of 0.2 g (0.97 mmol) of ethyl 5-fluoro-1H-indole-2-carboxylate, 0.178 g (1.45 mmol) of 2-(pyrid-3-yl)ethanol and 0.36 ml (1.44 mmol) of tributylphosphine in 30 ml of tetrahydrofuran. The reaction mixture is stirred overnight at room temperature and then concentrated under reduced pressure and taken up in 50 ml of cyclohexane. The suspension is then filtered and the filtrate is chromatographed on a column of silica (eluent: dichloromethane/methanol). 0.125 g of the expected product is obtained.

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationThe suspension is then filtered
  3. customthe filtrate is chromatographed on a column of silica (eluent: dichloromethane/methanol)

Sources & evidence

ORD record
ord-67c50f2d0a5c4efa86d731eef8274961
Source dataset
uspto-grants-2014_05
Patent number
US08735432B2

Reaction notes

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