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Triethylamine → 4-bromo-N-(2,4-dimethoxybenzyl) N-(3-(4-nitrophenyl)prop-2-ynyl)-1H-pyrrole-2-carboxamide

HRID 2096279
Notes
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Reaction equation

HRID 2096279 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:4]=1[CH2:5][NH:6][CH2:7][C:8]#[C:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1.[Br:25][C:26]1[CH:27]=[C:28]([C:31](O)=[O:32])[NH:29][CH:30]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O>[Br:25][C:26]1[CH:27]=[C:28]([C:31]([N:6]([CH2:5][C:4]2[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:3]=2[O:2][CH3:1])[CH2:7][C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[O:32])[NH:29][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27413814-bromo-1H-pyrrole-2-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 67443629N-(2,4-dimethoxybenzyl)-3-(4-nitrophenyl)prop-2-yn-1-amine

Product 1

HCID 67441092
4-bromo-N-(2,4-dimethoxybenzyl) N-(3-(4-nitrophenyl)prop-2-ynyl)-1H-pyrrole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of EXAMPLE 23B (1 g, 3.07 mmol) in anhydrous N,N-dimethylformamide (25 mL) was added 4-bromo-1H-pyrrole-2-carboxylic acid (0.67 g, 3.53 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (0.77 g, 4 mmol), 1-hydroxybenzotriazole hydrate (0.61 g, 4 mmol) and triethylamine (0.4 g, 4 mmol). The reaction was stirred at room temperature overnight, and partitioned between ethyl acetate and brine. The organic phase was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude material was purified flash chromatography (20% ethyl acetate in hexane) to afford the title compound. LC-MS (ESI): m/z 500, 498 (M+H), RT: 2.37 min; 1H NMR (400 MHz, dimethylsulfoxide-d6): δ 3.75 (s, 3H), 3.78 (s, 3H), 4.51 (s, 2H), 4.77 (s, 2H), 6.53 (dd, J=6.4, 2.0 Hz, 1H), 6.60 (d, J=2.0 Hz, 1H), 7.09 (dd, J=1.2, 1.6 Hz, 1H), 7.15 (d, J=8.0 Hz, 1H), 7.60 (d, J=8.8 Hz, 2H), 8.21 (d, J=9.2 Hz, 2H), 12.02 (br s, 1H).

Workup

  1. custompartitioned between ethyl acetate and brine
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified flash chromatography (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f9400102b1c54a09842c530e4bb8e1a6
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08450320B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes