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Hydrochloric Acid → 2-(1,5-dimethyl-1H-indol-7-yl)-N-[2-(6-fluoro-1H-indol-3-yl)-acetyl]-2-oxo-acetamide

HRID 2215786
Notes
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Reaction equation

HRID 2215786 reaction equation
CO[C:3](=[O:17])[C:4]([C:6]1[CH:7]=[C:8]([CH3:16])[CH:9]=[C:10]2[C:14]=1[N:13]([CH3:15])[CH:12]=[CH:11]2)=[O:5].[F:18][C:19]1[CH:27]=[C:26]2[C:22]([C:23]([CH2:28][C:29]([NH2:31])=[O:30])=[CH:24][NH:25]2)=[CH:21][CH:20]=1.CC(C)([O-])C.[K+].C1COCC1.Cl>CN(C=O)C>[CH3:15][N:13]1[C:14]2[C:10](=[CH:9][C:8]([CH3:16])=[CH:7][C:6]=2[C:4](=[O:5])[C:3]([NH:31][C:29](=[O:30])[CH2:28][C:23]2[C:22]3[C:26](=[CH:27][C:19]([F:18])=[CH:20][CH:21]=3)[NH:25][CH:24]=2)=[O:17])[CH:11]=[CH:12]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 219500622-(6-fluoro-1H-indol-3-yl)acetamideHCID 23665647Potassium tert-butoxideHCID 69642519(1,5-dimethyl-1H-indol-7-yl)-oxo-acetic acid methyl ester

Product 1

HCID 21950001
2-(1,5-dimethyl-1H-indol-7-yl)-N-[2-(6-fluoro-1H-indol-3-yl)-acetyl]-2-oxo-acetamide
Yield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (1,5-dimethyl-1H-indol-7-yl)-oxo-acetic acid methyl ester (0.51 g, 2.21 mmol) and 2-(6-fluoro-1H-indol-3-yl)-acetamide (0.38 g, 2 mmol) in DMF (20 mL) was added a solution of potassium tert-butoxide in THF (1.0 M, 8.0 mL, 8.0 mmol) at room temperature. The reaction mixture was stirred at room temperature for 11 h, treated with concentrated hydrochloric acid (2 mL) and then heated at 50° C. for 2 h. The mixture was cooled to room temperature, extracted with ethyl acetate and the extract was washed with water, saturated aqueous sodium bicarbonate and brine dried (sodium sulfate), filtered and evaporated. Flash column chromatography on silica gel eluting with chloroform and acetone gave 2-(1,5-dimethyl-1H-indol-7-yl)-N-[2-(6-fluoro-1H-indol-3-yl)-acetyl]-2-oxo-acetamide (170 mg, 23%) and 3-(1,5-dimethyl-1H-indol-7-yl)-4-(6-fluoro-1H-indol-3-yl)-pyyrole-2,5-dione (340 mg, 45.5%). 1H NMR (d6-DMSO, 400 MHz) δ 2.26 (s, 3H), 3.58 (s, 3H), 6.36 (d, J=3.13 Hz, 1H), 6.40˜6.45 (m, 2H), 6.73 (s, 1H), 7.11 (dd, J1=2.34 Hz, J2=9.38 Hz, 1H), 7.16 (d, J=3.13 Hz, 1H), 7.7.39 (s, 1H), 7.80 (d, J=3.13 Hz, 1H), 11.14 (s, 1H), 11.82 (s, 1H); MS (ES, m/z): C22H16FN3O2: 374.2 (M++1); 372.2 (M+−1).

Workup

  1. temperatureheated at 50° C. for 2 h
  2. temperatureThe mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washthe extract was washed with water, saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-40f619fe98774388be2ec1cdfcb8efb7
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07109229B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes