Hydrochloric Acid → HCID 59408991, compound

HRID 1894745Notes

Reaction equation

HRID 1894745 reaction equation
CO[C:3](=[O:17])[C:4]([C:6]1[C:14]2[C:9]3=[C:10]([CH2:15][CH2:16][N:8]3[CH:7]=1)[CH:11]=[CH:12][CH:13]=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+].Cl>O1CCCC1.C(OCC)(=O)C>[C:6]1([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)[C:14]2[C:9]3=[C:10]([CH2:15][CH2:16][N:8]3[CH:7]=1)[CH:11]=[CH:12][CH:13]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 397Indole-3-acetamideHCID 23665647Potassium tert-butoxideHCID 59408995HCID 59408995, compound

Product 1

HCID 59408991HCID 59408991, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4,5-dihydro-pyrrolo[3,2,1-hi]indol-1-yl)-oxo-acetic acid methyl ester (150 mg, 0.66 mmol) and 2-(1H-indol-3-yl)-acetamide (114 mg, 0.66 mmol) in anhydrous tetrahydrofuran (10 ml) at 0° C. was added potassium tert-butoxide (2.6 ml, 2.6 mmol; 1M solution in tetrahydrofuran). The mixture was stirred at room temperature for 1 hour before concentrated hydrochloric acid (3 ml) was added and the mixture stirred for an additional 20 minutes. The mixture was poured into ethyl acetate (200 ml) washed with water (700 ml) and brine (100 ml). The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by flash column chromatography (SiO2, 40% EtOAc in hexanes) to afford 3-(4,5-dihydro-pyrrolo[3,2,1-hi]indol-1-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione as a red solid (115 mg). 400 MHz 1H NMR (DMSO-d6) δ: 11.63 (s, 1H), 10.84 (s, 1H), 7.98 (s, 1H), 7.62 (d, J=2.8 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.05-7.01 (m, 2H), 6.78-6.74 (m, 2H), 6.53 (t, J=7.2 Hz, 1H), 6.08 (d, J=8.0 Hz, 1H), 4.58 (t, J=7.2 Hz, 2H), 3.71 (t, J=6.8 Hz, 2H); LCMS: 354 [M+H].

Workup

  1. additionwas added
  2. washwashed with water (700 ml) and brine (100 ml)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by flash column chromatography (SiO2, 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1040df1b92c949fabc12fda70e59666e
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

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