Trifluoroacetic acid → HCID 21129518, compound

HRID 1071051Notes

Reaction equation

HRID 1071051 reaction equation
[Br:1][C:2]1[C:3]2[C:4]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19][C:5]=3[N:6]([CH2:11][C:12]([O:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[O:13])[C:7]=2[CH:8]=[CH:9][CH:10]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]2[C:4]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19][C:5]=3[N:6]([CH2:11][C:12]([O:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[O:13])[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22396640HCID 22396640, compound

Product 1

HCID 21129518HCID 21129518, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 10-bromo-6-(2-isobutoxy-2-oxoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.0412 g, 0.0859 mmol) was dissolved in CH2Cl2 (2 mL) and trifluoroacetic acid (1.0 mL, 1.48 g, 13.0 mmol, 151 equiv.) was added. The resulting solution was stirred at rt for 2.5 h. The reaction mixture was concentrated to dryness. The residue was taken up in EtOAc (2 mL), then treated with 1N HCl in Et2O. Hydrochloride salt formation did not occur and the resulting solution were concentrated to dryness. The residue was partitioned between EtOAc and 1N NaOH. The layers were separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The crude isobutyl (10-bromo-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)acetate (0.0260 g) was obtained in 80% yield. 1H NMR (300 MHz, CD3OD) δ 0.85, 1.86, 2.98-3.03, 3.11-3.14, 3.53-3.56, 3.91, 5.02, 6.94, 7.18, 7.25; MS (ESI+) for C18H23BrN2O2 m/z 379.0 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additiontreated with 1N HCl in Et2O
  3. concentrationthe resulting solution were concentrated to dryness
  4. customThe residue was partitioned between EtOAc and 1N NaOH
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with EtOAc
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c1104751aeb8460e98e68ce8758a8f26
Source dataset
uspto-grants-2005_06
Patent number
US06903090B2

Reaction notes

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