Tributylphosphine → HCID 22570270, compound

HRID 23979Notes

Reaction equation

HRID 23979 reaction equation
N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[OH:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([CH2:29][CH:30]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:31]([O:33]C)=[O:32])=[CH:23]2.O[CH2:43][CH2:44][CH2:45][NH:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=1.C(P(CCCC)CCCC)CCC>O1CCCC1>[CH2:35]([CH:30]([CH2:29][C:24]1[NH:25][C:26]2[C:22]([CH:23]=1)=[CH:21][C:20]([O:19][CH2:43][CH2:44][CH2:45][NH:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=1)=[CH:28][CH:27]=2)[C:31]([OH:33])=[O:32])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 114124793-((Pyridin-2-yl)amino)propan-1-olHCID 69512901Methyl 3-(5-hydoxylindolyl)-2-benzylpropanoate

Product 1

HCID 22570270HCID 22570270, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1′-(Azodicarbonyl)dipiperidine (0.18 g, 0.7 mmol) was added to a solution of methyl 3-(5-hydoxylindolyl)-2-benzylpropanoate (0.12 g, 0.39 mmol), as prepared in the preceding step, 2-(3-hydroxypropyl)aminopyridine (0.07 g, 0.47 mmol), as prepared instep b of Example 1, and tri-n-butylphosphine (0.14 g, 0.7 mmol) in tetrahydrofuran (6.0 mL). After stirring at ambient temperature overnight (16 h), the reaction was concentrated in vacuo and the residue purified by flash chromatography on silica gel (10%-50% ethyl acetate in hexane) to give the title compound as a yellow oil (0.064 g, 38%). 1H-NMR (400 MHz, CDCl3) δ 8.08 (br s, 1H), 7.40 (m, 1H), 7.37 (m, 1H), 7.22 (m, 2H), 7.00 (m, 3H), 6.84 (dd, J=8.9, 2.4 Hz, 1H), 6.54 (m, 1H), 6.40 (d, J=8.4 Hz, 2H), 6.36 (d, J=3.1 Hz, 1H), 4.77 (br s, 1H), 4.40 (m, 1), 4.17 (m, 3H), 3.52 (m, 5H), 3.24 (m, 1), 3.08 (m, 1H), 2.76 (m, 1H), 2.11 (m, 2H).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customthe residue purified by flash chromatography on silica gel (10%-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bc9c3c6bb2f24bb284659d3ba0a2614a
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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