Methanol → HCID 59774848, compound

HRID 2387283Notes

Reaction equation

HRID 2387283 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]3[CH:15]=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:16]([S:19]([N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([CH:31]=[O:32])[CH:29]=2)[CH:24]=[CH:23]1)(=[O:21])=[O:20])[CH2:17][CH3:18].[OH-].[K+].CO>O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]3[C:15]([CH:31]([C:28]4[CH:29]=[C:30]5[C:25]([CH:24]=[CH:23][N:22]5[S:19]([CH2:16][CH2:17][CH3:18])(=[O:21])=[O:20])=[CH:26][CH:27]=4)[OH:32])=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 59774804HCID 59774804, compoundHCID 59774805HCID 59774805, compound

Product 1

HCID 59774848HCID 59774848, compoundYield 0%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a round bottom flask, was added 5-cyclopentyloxy-1H-pyrrolo[2,3-b]pyridine (P-0001, 0.110 g, 0.544 mol, prepared as describes in Example 12), 1-(propane-1-sulfonyl)-1H-indole-6-carbaldehyde (60, 0.169 g, 0.674 mol), potassium hydroxide (91.6 mg, 1.63 mol) and methanol (2 mL, 0.05 mol). The reaction was allowed to stir at room temperature overnight. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with a gradient of ethyl acetate (with 4% acetic acid) in hexanes to provide 88 mg of the desired compound. MS (EST) [M+H+]+=454.2.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography
  7. washeluting with a gradient of ethyl acetate (with 4% acetic acid) in hexanes

Sources & evidence

ORD record
ord-9f8c166085354fb389f4cd252f3fbddd
Source dataset
uspto-grants-2012_09
Patent number
US08268858B2

Reaction notes

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