Methanol → HCID 11502380, compound

HRID 506775Notes

Reaction equation

HRID 506775 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:20]3[N:28](S(C4C=CC(C)=CC=4)(=O)=O)[C:23]4=[N:24][CH:25]=[CH:26][CH:27]=[C:22]4[CH:21]=3)=[CH:10][N:11]([CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:6]2=[CH:5][C:4]=1[O:39][CH3:40].CO>[OH-].[K+]>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:20]3[NH:28][C:23]4=[N:24][CH:25]=[CH:26][CH:27]=[C:22]4[CH:21]=3)=[CH:10][N:11]([CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:6]2=[CH:5][C:4]=1[O:39][CH3:40]

Participants

4

Reactant 2

HCID 887MethanolHCID 46868292HCID 46868292, compound

Product 1

HCID 11502380HCID 11502380, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
55 °C

Procedure

Bring bisazaindole 19 (48 mg, 0.0856 mmol) to reflux in KOH at 3%/MeOH for 8 h, then continue heating at 55° C. for 16 h. The reaction medium is then concentrated under vacuum, the residue is diluted with EtOAc, washed with saturated NaHCO3, dried (MgSO4), and concentrated until a residual oil is obtained. The latter is submitted to flash chromatography to give 20 (19.7 mg, 56.6%) as a white solid: 1H NMR (CDCl3) δ 10.77 (s broad, 1H), 8.20 (d, 1H, J=4.5 Hz), 7.82 (d, 1H, J=7.5 Hz), 7.57 (s, 1H), 7.13 (s, 1H), 7.03 (m, 1H), 6.57 (d, 1H, J=1.5 Hz), 4.23 (s, 3H), 4.22 (t, 2H, J=6.6 Hz), 3.96 (s, 3H), 3.70 (t, 4H, J=4.6 Hz), 2.77 (t, 2H, J=6.4 Hz), 2.49 (t, 4H, J=4.6 Hz). TLC (MeOH at 4%/CH2Cl2, 0.25% of NH3) Rf=0.20, m/z obs.=408.26 (M+1).

Workup

  1. concentrationThe reaction medium is then concentrated under vacuum
  2. additionthe residue is diluted with EtOAc
  3. washwashed with saturated NaHCO3
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated until a residual oil
  6. customis obtained

Sources & evidence

ORD record
ord-f2a472598da8404282ae97dd01854794
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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