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Hydrochloric Acid → HCID 21949958, compound

HRID 2215759
Notes
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Reaction equation

HRID 2215759 reaction equation
CC([O-])(C)C.[K+].C1COCC1.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH2:21][C:22]([NH2:24])=[O:23])=[CH:13]1.C[O:26][C:27](=O)[C:28]([C:30]1[CH:31]=[CH:32][CH:33]=[C:34]2[C:38]=1[N:37]([CH2:39][CH3:40])[CH:36]=[CH:35]2)=O.Cl>CN(C=O)C.CCOC(C)=O>[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]2[C:22](=[O:23])[NH:24][C:27](=[O:26])[C:28]=2[C:30]2[CH:31]=[CH:32][CH:33]=[C:34]3[C:38]=2[N:37]([CH2:39][CH3:40])[CH:36]=[CH:35]3)=[CH:13]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 397Indole-3-acetamideHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 69642170HCID 69642170, compound

Product 1

HCID 21949958HCID 21949958, compoundYield 38.6%

Reagents, catalysts & solvents

2
HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A 1.0 M solution of KOtBu in THF (6 mL, 6 mmol) was added to a solution of 2-(1H-indol-3-yl)-acetamide (478 mg, 2.75 mmol) and (1-ethyl-1H-indol-7-yl)-oxo-acetic acid methyl ester (635 mg, 2.75 mmol) in DMF (20 mL). The deep red-orange solution was stirred 12 h at 50° C., allowed to cool, and 1N HCl added. The orange mixture was poured into EtOAc, and the EtOAc layer was separated and washed with 1N HCl, water, saturated NaHCO3 and brine, dried (MgSO4), filtered, and concentrated onto SiO2. Flash chromatography (1:1 EtOAc:hexanes) followed by precipitation from hot methanol afforded the title compound (377 mg, 37%) as a orange-red solid. Heating under vacuum at 70° C. afforded material which was used without further purification. 1H NMR (400 MHz, DMSO-d6) 11.83 (br s, 1H), 11.13 (s, 1H), 7.94 (d, J=3 Hz, 1H), 7.61 (dd, J=8, 1.5 Hz, 1H), 7.3 (m, 2H), 6.93–7.0 (m, 3H), 6.48 (m, 3H), 6.48 (m, 2H), 6.3 (d, J=7 Hz, 1H), 4.0 (m, 2H), 1.06 (t, J=5 Hz, 3H). MS (electrospray, m/z) 354 (M−−1).

Workup

  1. temperatureto cool
  2. customthe EtOAc layer was separated
  3. washwashed with 1N HCl, water, saturated NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated onto SiO2
  7. customFlash chromatography (1:1 EtOAc:hexanes) followed by precipitation from hot methanol

Sources & evidence

ORD record
ord-c4d714957b604b348e1f07749615d5e3
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