Trifluoroacetic acid → HCID 59238959, compound

HRID 1949125Notes

Reaction equation

HRID 1949125 reaction equation
C([N:8]1[C:20]2[C:19]([CH3:21])=[C:18]3[N:22](C(OC(C)(C)C)=O)[C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][C:28]=4[C:17]3=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([F:37])[CH:13]=2)(OC(C)(C)C)=O.FC(F)(F)C(O)=O>ClCCl>[F:29][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:18]1[C:19]([CH3:21])=[C:20]3[NH:8][C:9]4[CH:10]=[CH:11][C:12]([F:37])=[CH:13][C:14]=4[C:15]3=[CH:16][C:17]2=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67212019HCID 67212019, compound

Product 1

HCID 59238959HCID 59238959, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5,7-diBOC-2,10-difluoro-6-methylindolo[2,3-b]carbazole (4.45 g, 8.8 mmol) was stirred with a solution of 20% trifluoroacetic acid in dichloromethane (100 mL) at room temperature for two hours. The solvents were evaporated and the residue dissolved in ethyl acetate (200 mL). This was washed with saturated sodium bicarbonate solution (100 mL) and dried over magnesium sulfate. After evaporation of the solvent, the residue was chromatographed on silica gel, eluting with a gradient of dichloromethane and hexane (50% dichloromethane to 100% dichloromethane) to give 2,10-difluoro-6-methyl-5,7-dihydro-indolo[2,3-b]carbazole (2.4 g, 90% yield). 1H NMR (300 MHz) (DMSO-d6) δ 11.05 (2H, s, —NH), 8.67 (1H, s, arom), 7.89 (2H, dd, J=9.5, 2.6 Hz, arom), 7.43 (2H, dd, J=8.9, 4.4 Hz, arom), 7.17 ppm (2H, dt, J=9.5, 2.6 Hz, arom) and 2.70 ppm (3H, s, —CH3).

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe residue dissolved in ethyl acetate (200 mL)
  3. washThis was washed with saturated sodium bicarbonate solution (100 mL)
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed on silica gel
  7. washeluting with a gradient of dichloromethane and hexane (50% dichloromethane to 100% dichloromethane)

Sources & evidence

ORD record
ord-713552eaac5a499d8913d4b00012718f
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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