Trifluoroacetic acid → HCID 86585356, compound

HRID 2307069Notes

Reaction equation

HRID 2307069 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:17]=[CH:16][C:15]2[N:14]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13]3[CH2:24][CH2:25][N:26](C(OC(C)(C)C)=O)[CH2:27][CH2:28][C:12]=3[C:11]=2[C:10]=1[Cl:36].[OH-].[Na+]>C(Cl)Cl>[Cl:8][C:9]1[CH:17]=[CH:16][C:15]2[N:14]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13]3[CH2:24][CH2:25][NH:26][CH2:27][CH2:28][C:12]=3[C:11]=2[C:10]=1[Cl:36]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 22396818tert-Butyl 9,10-dichloro-6-(2-ethoxy-2-oxoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

Product 1

HCID 86585356HCID 86585356, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (10.5 mL, 136 mmol) was added to a solution of tert-butyl 9,10-dichloro-6-(2-ethoxy-2-oxoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (3.0 g, 6.8 mmol) in CH2Cl2 (70 mL). After 5 h, the reaction was made basic with 10% aqueous NaOH and extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, decanted, and concentrated to give 2.4 g of the crude yellow oil: 1H NMR (300 MHz, CDCl3) δ 7.16 (d, J=8.7 Hz, 1H), 6.97 (d, J=8.7 Hz, 1H), 4.75 (s, 2H), 4.19 (q, J=7.1 Hz, 2H), 3.45 (m, 2H), 3.10 (t, J=5.1 Hz, 4H), 2.87 (m, 2H 2.28 (br s, 1H) 1.25 (m, 3H); IR (diffuse reflectance) 2979, 2958, 2939, 2904, 2837, 2816, 2797, 2766, 2644, 1744, 1449, 1372, 1279, 1204, 1160 cm−1;MS (EI) m/z 340 (M+), 305, 300, 298, 270, 226, 224, 154, 149, 127; HRMS (FAB) calcd for C16H18CL2N2O2+H 341.0823, found 341.0818.

Workup

  1. extractionextracted with CH2Cl2 (3×50 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customdecanted
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-388ee82db1ab4395adc940f1b1c3341b
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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