Pyridine → HCID 57559127, compound

HRID 37972Notes

Reaction equation

HRID 37972 reaction equation
[CH2:1]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[CH:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:4][NH:3][CH2:2]1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1C=CC=CC=1>C(Cl)Cl>[CH2:18]([O:17][C:15]([CH:5]1[C:6]2[NH:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]=2[CH2:1][CH2:2][N:3]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:4]1)=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 57559105Ethyl 1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate

Product 1

HCID 57559127HCID 57559127, compoundYield 7.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of ethyl 1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate (520 mg, 2 mmol), cupric acetate (728 mg, 4 mmol), phenyl boronic acid (490 mg, 4 mol) and pyridine (0.35 mL, 4 mmol) in dry DCM (20 mL) was stirred at ambient temperature for 3 days. The mixture was filtered though a pad of celite. The filtrate was concentrated in vacuo and then purified by chromatography on silica gel eluting with EtOAc-Hexane (7:93) to give the title compound (53 mg); 1H-NMR (CDCl3): δ 8.66 (1H, s), 7.42 (1H, d), 7.26-7.18 (4 h, m), 7.10-7.00 (2H, m), 7.69 (2H, m), 6.67 (1H, t), 5.22 (1H, m), 4.40-4.18 (3H, m), 4.04-4.01 (1H, m), 3.98-3.88 (1H, m), 3.58-3.52 (1H, m), 3.22-3.15 (1H, m), 3.08-3.02 (1H, m), 1.27 (3H, t); MS (ES): 335 (MH+).

Workup

  1. filtrationThe mixture was filtered though a pad of celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. custompurified by chromatography on silica gel eluting with EtOAc-Hexane (7:93)

Sources & evidence

ORD record
ord-c26cd63bdca4417d9d003932ad5a0d9a
Source dataset
uspto-grants-2013_09
Patent number
US08524704B2

Reaction notes

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