5-Fluoroindole-2-carboxylic acid → HCID 22065999, compound

HRID 1768345Notes

Reaction equation

HRID 1768345 reaction equation
[N:1]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([C:25](O)=[O:26])=[CH:19]2.CCN=C=NCCCN(C)C>C(Cl)Cl>[F:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([C:25]([N:4]1[CH2:5][CH2:6][CH2:7][N:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:2][CH2:3]1)=[O:26])=[CH:19]2

Participants

5

Reactant 3

HCID 18205-Fluoroindole-2-carboxylic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 22065999HCID 22065999, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 1,4-diazepane-1-carboxylate (2.0 g, 10 mmol, Aldrich), 5-fluoro-1H-indole-2-carboxylic acid (1.79 g, 10 mmol, Aldrich), and EDCI (1.92 g, 10 mmol) were combined in CH2Cl2 (30 mL) at room temperature and stirred for 24 hours. The mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (5% MeOH/CH2Cl2) to provide the title compound. 1H NMR (CD3OD, 300 MHz) δ 1.46(s, 9H), 1.86–2.14(m, 2H), 3.40–3.58(m, 2H), 3.62–3.72(m, 2H), 3.75–4.05(m, 4H), 6.78(s, 1H), 6.99–7.09(m, 1H), 7.28–7.35(m, 2H); MS (DCI/NH3) m/z 362 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-8758b23068544b998dcd210a5c6f4bf4
Source dataset
uspto-grants-2007_06
Patent number
US07235661B2

Reaction notes

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