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

HRID 1880657Notes

Reaction equation

HRID 1880657 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-95f0778b2d074177a29252fa84d945cf
Source dataset
uspto-grants-2012_11
Patent number
US08318775B2

Reaction notes

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