Diisopropylethylamine → 5-(4-Morpholin-4-yl-piperidine-1-carbonyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 1820490Notes

Reaction equation

HRID 1820490 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]([OH:17])=O)=[CH:10][CH:9]=2)=[O:5].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[NH:40]1[CH2:45][CH2:44][CH:43]([N:46]2[CH2:51][CH2:50][O:49][CH2:48][CH2:47]2)[CH2:42][CH2:41]1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH2:2]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]([N:40]1[CH2:45][CH2:44][CH:43]([N:46]3[CH2:51][CH2:50][O:49][CH2:48][CH2:47]3)[CH2:42][CH2:41]1)=[O:17])=[CH:10][CH:9]=2)=[O:5])[CH3:1]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 7957244-MorpholinopiperidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 180713652-(Ethoxycarbonyl)-1H-indole-5-carboxylic acid

Product 1

HCID 686819405-(4-Morpholin-4-yl-piperidine-1-carbonyl)-1H-indole-2-carboxylic acid ethyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized in analogy to example 1, intermediate a), from 1H-indole-2,5-dicarboxylic acid 2-ethyl ester, O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (commercially available), 4-(piperidin-4-yl)-morpholine (commercially available) and N,N-diisopropylethylamine in N,N-dimethylformamide, to give the desired product as a light yellow foam (72%).

Sources & evidence

ORD record
ord-62897f9df26b476a8fb42121cffdf26a
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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