Diethylethanolamine → N,N-Diethyl-2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]ethan-1-amine
Reaction equation
[N:1]1([CH2:7][CH2:8]O)[CH2:6][CH2:5]O[CH2:3][CH2:2]1.[CH2:10]([N:12]([CH2:16][CH3:17])[CH2:13][CH2:14][OH:15])[CH3:11].[CH2:18]([N:20]([CH2:25][CH3:26])[CH2:21][CH2:22][CH2:23][OH:24])[CH3:19].[N:27]1([CH2:33][CH2:34][OH:35])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.[N:36]1([CH2:41][CH2:42][OH:43])[CH2:40][CH2:39][CH2:38][CH2:37]1>>[CH2:10]([N:12]([CH2:16][CH3:17])[CH2:13][CH2:14][O:15][C:22]1[CH:23]=[C:8]2[CH:5]=[CH:6][NH:1][C:7]2=[N:20][CH:21]=1)[CH3:11].[CH2:18]([N:20]([CH2:25][CH3:26])[CH2:21][CH2:22][CH2:23][O:24][C:29]1[CH:30]=[C:31]2[CH:38]=[CH:37][NH:36][C:32]2=[N:27][CH:28]=1)[CH3:19].[N:27]1([CH2:33][CH2:34][O:35][C:3]2[CH:23]=[C:22]3[CH:26]=[CH:25][NH:20][C:21]3=[N:1][CH:2]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.[N:36]1([CH2:41][CH2:42][O:43][C:29]2[CH:30]=[C:31]3[CH:3]=[CH:2][NH:1][C:32]3=[N:27][CH:28]=2)[CH2:40][CH2:39][CH2:38][CH2:37]1Participants
9
Reactant 5
Product 4
Procedure
Additional 5-substituted 7-azaindoles were prepared following the protocol of Scheme 31, replacing 4-morpholineethanol with either 2-diethylamino-ethanol, 3-diethylamino-propan-1-ol, 2-piperidin-1-yl-ethanol, or 2-pyrrolidin-1-yl-ethanol to provide diethyl-[2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-ethyl]-amine, Diethyl-[3-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-propyl]-amine, 5-(2-piperidin-1-yl-ethoxy)-1H-pyrrolo[2,3-b]pyridine, and 5-(2-pyrrolidin-1-yl-ethoxy)-1H-pyrrolo[2,3-b]pyridine, respectively.
Sources & evidence
- ORD record
- ord-3880541291644c748567055bccbe16e6
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07846941B2
Reaction notes
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