Dimethylformamide → 2-((E)-2-(dimethylamino)vinyl)-1-methyl-5-nitro-1H-indole-3-carbaldehyde

HRID 2375301

반응식

HRID 2375301 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH3:13])=[C:7]2[CH:14]=[O:15])([O-:3])=[O:2].CO[CH:18](OC)[N:19]([CH3:21])[CH3:20].[CH3:24]N(C=O)C>>[CH3:18][N:19]([CH3:21])/[CH:20]=[CH:13]/[C:8]1[N:9]([CH3:24])[C:10]2[C:6]([C:7]=1[CH:14]=[O:15])=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 6093592-methyl-5-nitro-1H-indole-3-carbaldehyde

생성물 1

HCID 8672342-((E)-2-(dimethylamino)vinyl)-1-methyl-5-nitro-1H-indole-3-carbaldehyde

반응 조건

온도
100 °C

실험 절차

5-nitro-2-methyl-1H-indole-3-carbaldehyde (200 mg, 0.98 mmol) was dissolved in 5 mL dry DMF, followed by the addition of N,N-dimethylformamide dimethyl acetal (467 mg, 521 □L, 3.92 mmol). The reaction mixture was heated to 100° C. for 2 h and turned from light yellow to dark red over the course of the reaction. The crude reaction was concentrated in vacuo to obtain a red solid. The crude solid was washed with 5:1 EtOAc/hexane (6×10 mL), followed by hexane (2×10 mL) to obtain 2-((E)-2-(dimethylamino)vinyl)-1-methyl-5-nitro-1H-indole-3-carbaldehyde as a brick red solid (215 mg, 85% yield). 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 C14H15N3O3=273.11; Found 274.00. 1H NMR (400 mHz, DMSO-d6) δ 9.80 (s, 1H), 8.03 (dd, J=8.9, 2.4 Hz, 1H), 7.58 (d, J=9.0 Hz, 1H), 7.58 (m, 2H), 5.25 (d, J=13.0 Hz, 1H), 3.72 (s, 3H), 3.03 (s, 6H).

후처리

  1. customover the course of the reaction
  2. customThe crude reaction
  3. concentrationwas concentrated in vacuo
  4. customto obtain a red solid
  5. washThe crude solid was washed with 5:1 EtOAc/hexane (6×10 mL)

출처 및 근거

ORD 기록
ord-9ffcb73db1da414bbe8db9871e61867b
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465738B2

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