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Indole-3-acetamide → HCID 21950068, compound

HRID 2215791
Notes
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Reaction equation

HRID 2215791 reaction equation
CO[C:3](=[O:17])[C:4]([C:6]1[CH:7]=[C:8]([F:16])[CH:9]=[C:10]2[C:14]=1[N:13]([CH3:15])[CH:12]=[CH:11]2)=O.[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([CH2:27][C:28]([NH2:30])=[O:29])=[CH:19]1.CC(C)([O-])C.[K+].C1COCC1>CN(C=O)C>[CH3:15][N:13]1[C:14]2[C:10](=[CH:9][C:8]([F:16])=[CH:7][C:6]=2[C:4]2[C:3](=[O:17])[NH:30][C:28](=[O:29])[C:27]=2[C:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[NH:18][CH:19]=2)[CH:11]=[CH:12]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 397Indole-3-acetamideHCID 8028TetrahydrofuranHCID 21055225HCID 21055225, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21950068HCID 21950068, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
55 °C

Procedure

To a mixture of (1-methyl-5-fluoro-1H-indol-7-yl)-oxo-acetic acid methyl ester (0.94 g, 4.0 mmol) and 2-(1H-indol-3-yl-acetamide (0.63 g, 3.64 mmol) in DMF (36 mL) was added a solution of potassium tert-butoxide in THF (1.0 M, 14.6 mL, 14.6 mmol) at room temperature. The reaction mixture was heated at 55° C. for 18 h, cooled to room temperature, and quenched with hydrochloric acid (conc.). After stirring at room temperature for 30 min, the mixture was extracted with ethyl acetate and the extract washed with water, saturated aqueous sodium bicarbonate and brine, dried (sodium sulfate), filtered and concentrated. Flash column chromatography on silica gel eluting with chloroform and acetone gave 3-(1-methyl-5-fluoro-1H-indol-7-yl)-4-(1H-indol-3-yl]-pyrrole-2,5-dione (0.72 mg, 55%). 1H NMR (d6-DMSO, 400 MHz) 3.67 (s, 3H), 6.34 (d, J=7.82 Hz, 1H), 6.48 (d, J=3.12 Hz, 1H), 6.54 (t, J=7.62 Hz, 1H), 6.77 (dd, J1=2.34 Hz, J2=9.77 Hz, 1H), 6.99 (t, J=7.42 Hz, 1H), 7.33˜7.42 (m, 3H), 7.97 (d, J=3.13 Hz, 1H), 11.20 (s, 1H), 11.93 (s, 1H); MS (ES, m/z): C21H14FN3O2: 360.15 (M++1), 358.23 (M+−1).

Workup

  1. temperaturecooled to room temperature
  2. customquenched with hydrochloric acid (conc.)
  3. extractionthe mixture was extracted with ethyl acetate
  4. washthe extract washed with water, saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ed029171c7a445f49039626157be57bf
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07109229B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes