Dimethylformamide → HCID 21949982, compound

HRID 2215833Notes

Reaction equation

HRID 2215833 reaction equation
CC([O-])(C)C.[K+].C1COCC1.[CH3:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[CH2:22][C:23]([NH2:25])=[O:24])[CH:15]=[CH:14]1.CO[C:28](=[O:49])[C:29]([C:31]1[C:39]2[C:34](=[C:35]([CH2:40][NH:41][C:42]([O:44]C(C)(C)C)=O)[CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1)=O.[CH3:50][N:51](C=O)[CH3:52]>>[CH3:50][N:51]([CH3:52])[C:42]([NH:41][CH2:40][C:35]1[CH:36]=[CH:37][CH:38]=[C:39]2[C:34]=1[NH:33][CH:32]=[C:31]2[C:29]1[C:28](=[O:49])[NH:25][C:23](=[O:24])[C:22]=1[C:20]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:21]=1[N:13]([CH3:12])[CH:14]=[CH:15]2)=[O:44]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 114353972-(1-methyl-1H-indol-7-yl)acetamideHCID 23665647Potassium tert-butoxideHCID 69642589HCID 69642589, compound

Product 1

HCID 21949982HCID 21949982, compoundYield 14%

Conditions

Temperature
140 °C

Procedure

A 1.0 M solution of KOtBu in THF (4.77 ml, 4.77 mmol) was added to a solution of 2-(1-methyl-1H-indol-7-yl-acetamide (0.3 g, 1.59 mmol) and [7-(tert-Butoxycarbonylamino-methyl)-1H-indol-3-yl]-oxo-acetic acid methyl ester (0.53 g, 1.59 mmol) in DMF (15 ml) at room temperature. The reaction was heated at 140° C. for 4 h, allowed to cool to room temperature quenched with pH 7 buffer. The mixture was poured into EtOAc, extracted, washed with saturated aq NaHCO3, brine, dried (MgSO4), filtered, and concentrated onto SiO2. Flash chromatography (50:50 ethyl acetate: hexanes) afforded the title compound (0.1 g, 14%) as an orange solid. MS (electrospray, m/z) 442.2 (M++1), 440.3 (M−−1).

Workup

  1. temperatureto cool to room temperature
  2. customquenched with pH 7 buffer
  3. additionThe mixture was poured into EtOAc
  4. extractionextracted
  5. washwashed with saturated aq NaHCO3, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated onto SiO2

Sources & evidence

ORD record
ord-617c2cdd3c9c421e800da0e4f4e852b8
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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