Dichloromethane → HCID 22396903, compound

HRID 2306942Notes

Reaction equation

HRID 2306942 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([Br:20])[C:14]=2[C:13]2[CH2:21][CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24][CH2:25][C:12]1=2.FC(F)(F)C(O)=O.C(Cl)[Cl:41]>>[ClH:41].[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([Br:20])[C:14]=2[C:13]2[CH2:21][CH2:22][NH:23][CH2:24][CH2:25][C:12]1=2

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 22396564HCID 22396564, compound

Product 1

HCID 22396903HCID 22396903, compound

Procedure

tert-Butyl 6-(1H-benzimidazol-2-ylmethyl)-10-bromo-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.105 g, 0.212 mmol) was dissolved in CH2Cl2 (5 mL) and trifluoroacetic acid (2.0 mL, 2.96 g, 26.0 mmol, 122 equiv.) was added. This mixture was stirred at rt in a capped vessel for 2.5 h. The reaction mixture was concentrated to dryness. The residue was taken up in EtOAc (2 mL), and 1M HCl in Et2O was added. The hydrochloride salt was collected by filtration and dried under vacuum. 6-(1H-benzimidazol-2-ylmethyl)-10-bromo-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole hydrochloride (0.943 g) was produced in quantitative yield. 1H NMR (300 MHz, DMF) δ 3.61-3.70, 3.83-3.86, 6.12, 7.06, 7.31, 7.36-7.42, 7.66-7.74, 7.74; 1H NMR (300 MHz, CD3OD) δ 3.33-3.36, 3.54-3.59, 3.83-3.86, 6.04, 7.09, 7.35, 7.41, 7.54-7.57, 7.71-7.74; MS (ESI+) for C20H19BrN4 m/z 395, 396.9 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. addition1M HCl in Et2O was added
  3. filtrationThe hydrochloride salt was collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ccfd4958758e400f82ec69cdd4567ed1
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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