Sodium Hydroxide → HCID 59836067, compound

HRID 2389024Notes

Reaction equation

HRID 2389024 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]=[C:11]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])=[CH:16][N:15](S(C3C=CC(C)=CC=3)(=O)=O)[C:12]2=[N:13][CH:14]=1.[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]=[C:11]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])=[CH:16][NH:15][C:12]2=[N:13][CH:14]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59836181HCID 59836181, compound

Product 1

HCID 59836067HCID 59836067, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2,7-Bis-(2-methoxy-phenyl)-5-(toluene-4-sulfonyl)-5H-pyrrolo[2,3-b]pyrazine (200 mg, 0.412 mmol) in MeOH (5 mL) was added a solution of NaOH (66 mg, 1.65 mmol) in water (200 μL). The mixture was stirred at room temperature for 3.5 hours before the solvents were removed. The resulting yellow residue was then purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes to afford 2,7-Bis-(2-methoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine (43 mg, 32% yield) as a pale yellow solid. 1H-NMR (500 MHz, CD3OD) δ 12.21 (s br, 1H), 8.80 (dd, 6.0 Hz, 1.75 Hz, 1H), 8.69 (s, 1H), 7.76 (dd, 6.0 Hz, 1.75 Hz, 1H), 7.43 (dt, 7.5 Hz, 1.75 Hz, 1H), 7.20 (m, 2H), 7.13 (m, 2H), 7.04 (t, 7.3 Hz, 1H), 3.92 (s, 3H), 3.85 (s, 3H). MS: m/z 332.1 [MH+].

Workup

  1. customwere removed
  2. customThe resulting yellow residue was then purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-71655a98e6fd4fcdb5276b87c1a5c6f2
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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