Trifluoroacetic acid → 2-[1,4]diazepan-1-yl-1-phenyl-1H-indole-3-carboxaldehyde

HRID 1678146Notes

Reaction equation

HRID 1678146 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:16]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:17]3[C:22]([C:23]=2[CH:24]=[O:25])=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[N:11]1([C:15]2[N:16]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:17]3[C:22]([C:23]=2[CH:24]=[O:25])=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 865968104-(3-formyl-1-phenyl-1H-indole-2-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 597547512-[1,4]diazepan-1-yl-1-phenyl-1H-indole-3-carboxaldehydeYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-Formyl-1-phenyl-1H-indole-2-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (1.06 g, 2.53 mmol) and trifluoroacetic acid (10 mL) in dichloromethane (4 mL) is stirred overnight at room temperature. The solvent is evaporated off and the residue dissolved in dichloromethane (10 mL), washed with 5% aq sodium carbonate, with water, with brine, dried, filtered and concentrated. The residue is purified by chromatography eluting with dichloromethane-5 to 10% methanol. Product containing fraction are combined and concentrated to afford 2-[1,4]diazepan-1-yl-1-phenyl-1H-indole-3-carboxaldehyde (86% yield) as a white solid. LC/MS: MS 320 (M+H); 2.5 min; NMR (CDCl3) 10.30 (1H, s), 8.25 (1H, d), 7.03-7.70 (7H, m), 6.97 (1H, d), 3.20-3.46 (4H, m), 2.84 (4H, m) 1.62(2H, m).

Workup

  1. customThe solvent is evaporated off
  2. dissolutionthe residue dissolved in dichloromethane (10 mL)
  3. washwashed with 5% aq sodium carbonate, with water, with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by chromatography
  8. washeluting with dichloromethane-5 to 10% methanol
  9. additionProduct containing fraction
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-62d5fa9ef8f844e0ba39af953f7b1308
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

Loading…