HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

ethyl 4-(3-(((benzyloxy)carbonyl)amino)-2-methylphenyl)-7-bromo-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylate → ethyl 4-(3-(((benzyloxy)carbonyl)amino)-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxylate

HRID 2361403
Notes
Print preview

Reaction equation

HRID 2361403 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:38])=[C:14]([CH:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([Br:31])=[CH:27][CH:28]=4)[NH:23][C:22]=3[CH:21]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[NH:20][CH:19]2[CH3:37])[CH:15]=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:38])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([Br:31])=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[N:20][C:19]=2[CH3:37])[CH:15]=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 67994581ethyl 4-(3-(((benzyloxy)carbonyl)amino)-2-methylphenyl)-7-bromo-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylate

Product 1

HCID 67995215ethyl 4-(3-(((benzyloxy)carbonyl)amino)-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxylateYield 32%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 7237O-XyleneSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

A solution of ethyl 4-(3-(((benzyloxy)carbonyl)amino)-2-methylphenyl)-7-bromo-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylate (4.68 g, 8.12 mmol) and 10% palladium on carbon (2.59 g, 2.44 mmol) in xylene (130 mL) was heated at 120° C. overnight. The reaction mixture was diluted with ethyl acetate and filtered through a pad of CELITE®. The CELITE® pad was washed well with ethyl acetate, and the filtrate was concentrated under reduced pressure. The residue was purified by flash silica gel chromatography using a mixture of ethyl acetate in hexane (20%-35%-50%) to give ethyl 4-(3-(((benzyloxy)carbonyl)amino)-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxylate (1.49 g, 2.60 mmol, 32% yield) as a burgundy solid. LC/MS M+1=572.2 and 574.2.

Workup

  1. filtrationfiltered through a pad of CELITE®
  2. washThe CELITE® pad was washed well with ethyl acetate
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by flash silica gel chromatography
  5. additiona mixture of ethyl acetate in hexane (20%-35%-50%)

Sources & evidence

ORD record
ord-b41f55783afe4136a4f04b72f6790a8d
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08685969B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes