Dimethylformamide → HCID 59854617, compound

HRID 2375300Notes

Reaction equation

HRID 2375300 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[C:5]2[CH:12]=[O:13].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18].[CH3:22]N(C=O)C>>[CH3:16][N:17]([CH3:19])/[CH:18]=[CH:11]/[C:6]1[N:7]([CH3:22])[C:8]2[C:4]([C:5]=1[CH:12]=[O:13])=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 64841155-Fluoro-2-methyl-1H-indole-3-carbaldehyde

Product 1

HCID 59854617HCID 59854617, compoundYield 62%

Conditions

Temperature
80 °C

Procedure

5-fluoro-2-methyl-1H-indole-3-carbaldehyde (50 mg, 0.28 mmol) was dissolved in 3 mL dry DMF, followed by the addition of N,N-dimethylformamide dimethyl acetal (124 mg, 138 μL, 1.04 mmol). The reaction mixture was heated to 80° C. for 4 h and turned from light yellow to dark red over the course of the reaction. The crude reaction was concentrated in vacuo, dissolved in 0.5 mL DMSO/MeOH, and purified by reverse phase HPLC (5-95% water/acetonitrile gradient over 60 minutes) to obtain 2-((E)-2-(dimethylamino)vinyl)-5-fluoro-1-methyl-1H-indole-3-carbaldehyde as a pale yellow solid (40 mg, 62% yield). 1H NMR (400 mHz, DMSO-d6) δ 9.73 (s, 1H), 7.73 (dd, J=9.8, 2.6 Hz, 1H), 7.39 (m, 2H), 6.96 (dt, J=9.2, 2.6 Hz, 1H), 5.20 (d, J=13.1 Hz, 1H), 3.66 (s, 3H), 2.99 (s, 6H). Mass and purity were confirmed by LC/MS using an acetonitrile gradient with 5 mM ammonium formate pH 6.5. Theoretical (M+H)+ m/z for C14H15FN2O=247.12; Found 247.06.

Workup

  1. customover the course of the reaction
  2. customThe crude reaction
  3. concentrationwas concentrated in vacuo
  4. dissolutiondissolved in 0.5 mL DMSO/MeOH
  5. custompurified by reverse phase HPLC (5-95% water/acetonitrile gradient over 60 minutes)

Sources & evidence

ORD record
ord-6b4e0ef11fe540deae45f4e71049bf67
Source dataset
uspto-grants-2008_12
Patent number
US07465738B2

Reaction notes

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