Dichloromethane → (E)-3-(3-((Dimethylamino)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acrylic acid hydrochloride

HRID 633983Notes

Reaction equation

HRID 633983 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]([CH2:11][C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18](/[CH:21]=[CH:22]/[C:23]([O:25]C(C)(C)C)=[O:24])[CH:19]=2)[NH:14][CH:13]=1)[CH3:10].[Cl:30]CCl>>[ClH:30].[CH3:8][N:9]([CH2:11][C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])[CH:19]=2)[NH:14][CH:13]=1)[CH3:10]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68338029HCID 68338029, compound

Product 1

HCID 70926878(E)-3-(3-((Dimethylamino)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acrylic acid hydrochloride

Procedure

Trifluoroacetic acid (2 mL) was added to a suspension of (E)-tert-butyl 3-(3-((dimethylamino)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acrylate (120 mg, 0.39 mmol) in dichloromethane (2 mL). The reaction mixture was stirred at room temperature for 30 minutes and concentrated to dryness. The resulting residue was solubilized in a solution of hydrochloric acid in dioxane (4N, 2 mL). After 10 minutes stirring at room temperature, the precipitate was filtered and washed with diethyl ether to afford the title product as a pale yellow solid (112 mg, quantitative).

Workup

  1. concentrationconcentrated to dryness
  2. stirringAfter 10 minutes stirring at room temperature
  3. filtrationthe precipitate was filtered
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-5b43b42830c443c790e4453b57221f79
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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