N,N,N',N'-Tetramethylethylenediamine → (1-Tert.butoxycarbonyl 5-aza 2-indolyl) (3-diethylaminocarbonyl 2-methoxy 4-pyridyl)methanol

HRID 1089914Notes

Reaction equation

HRID 1089914 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][N:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[Li])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([N:20]([CH2:33][CH3:34])[C:21]([C:23]1[C:24]([O:31][CH3:32])=[N:25][CH:26]=[CH:27][C:28]=1[CH:29]=[O:30])=[O:22])[CH3:19].CN(C)CCN(C)C.CC1(C)CCCC(C)(C)N1>>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][N:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH:29]([C:28]1[CH:27]=[CH:26][N:25]=[C:24]([O:31][CH3:32])[C:23]=1[C:21]([N:20]([CH2:18][CH3:19])[CH2:33][CH3:34])=[O:22])[OH:30])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 130352,2,6,6-TetramethylpiperidineHCID 11806629N,N-Diethyl-4-formyl-2-methoxynicotinamideHCID 178506646HCID 178506646, compound

Product 1

HCID 14476670(1-Tert.butoxycarbonyl 5-aza 2-indolyl) (3-diethylaminocarbonyl 2-methoxy 4-pyridyl)methanol

Procedure

Starting from 1-tert.butoxycarbonyl 2-lithio 5-aza indole and 3-diethylaminocarbonyl 4-formyl 2-methoxy pyridine as reagent with electrophilic character, prepared according to paragraph b (stabilization reagent: tetramethylethylenediamine; amine: 2,2,6,6-tetramethylpiperidine).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-543a3a3d03ff48d59fe23302b7790343
Source dataset
uspto-grants-1992_01
Patent number
US05079363

Reaction notes

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