Methanol → HCID 57891748, compound

HRID 1820907Notes

Reaction equation

HRID 1820907 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]#[C:11][C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH:5]=1.CO>[OH-].[Na+].O>[CH3:30][O:29][C:23]1[CH:22]=[C:21]([C:18]2[CH:19]=[C:20]3[C:12]([C:11]#[C:10][C:6]4[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=4)[C:3]([OH:31])=[O:2])=[CH:13][NH:14][C:15]3=[N:16][CH:17]=2)[CH:26]=[CH:25][C:24]=1[O:27][CH3:28]

Participants

5

Reactant 2

HCID 887MethanolHCID 57891691HCID 57891691, compound

Product 1

HCID 57891748HCID 57891748, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Into a microwave safe tube, 3-[5-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-3-ylethynyl]-benzoic acid methyl ester (0.049 g, 0.00012 mol) was dissolved in 5.00 M of Sodium hydroxide in Water (1.78 mL) and Methanol (7.1 mL, 0.18 mol). The reaction was warmed at 60 watts to 100° C. for 10 minutes. The resulting clear yellow solution was concentrated under reduced pressure. The resulting aqueous slurry was acidified to pH 5 with 1 M HCl (aq) and was extracted into ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, then concentrated under reduced pressure. The resulting residue was recrystalized from ethyl acetate and methanol to yield the titled compound as a white solid. MS(ESI) [M+H+]+=399.20

Workup

  1. temperatureThe reaction was warmed at 60 watts to 100° C. for 10 minutes
  2. concentrationThe resulting clear yellow solution was concentrated under reduced pressure
  3. extractionwas extracted into ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was recrystalized from ethyl acetate and methanol

Sources & evidence

ORD record
ord-c349d61e042e43358b1a9df835d96480
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

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