Triethylamine → HCID 68695984, compound

HRID 2264887Notes

Reaction equation

HRID 2264887 reaction equation
CC1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=3)NCC[C:5]2=1.CC[N:24]([CH2:27][CH3:28])[CH2:25][CH3:26].[Br:29][CH2:30][C:31](Br)=[O:32]>C1COCC1>[Br:29][CH2:30][C:31]([N:24]1[CH2:25][CH2:26][C:3]2[C:4]3[C:12](=[CH:13][CH:14]=[C:10]([CH2:9][C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=4)[CH:5]=3)[NH:11][C:28]=2[CH2:27]1)=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 59597173HCID 59597173, compound

Product 1

HCID 68695984HCID 68695984, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-methyl-1-(3-hydroxyphenyl)-1,2,3,4-tetrahydro-beta-carboline (1 equiv) in THF was added Et3N (2.2 equiv) and alpha-bromoacetyl bromide (1.2 equiv). The solution was stirred at room temperature for 30 min to give crude 2-bromo-1-[1-(3-hydroxyphenyl)-6-methyl-(1,2,3,4-tetrahydro-beta-carbolin-2-yl)]ethan-1-one. To the solution was added morpholine (2 equiv). The solution was stirred overnight and purified to give 3-[6-methyl-2-(morpholin-4-ylacetyl)-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl]phenol 16.

Sources & evidence

ORD record
ord-3c931b9dfd164dbfb17338c435641915
Source dataset
uspto-grants-2010_12
Patent number
US07855295B2

Reaction notes

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