Dimethylformamide → HCID 1207821, compound

HRID 2375303Notes

Reaction equation

HRID 2375303 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]#[N:12])=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=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:1]/[C:2]1[N:3]([CH3:24])[C:4]2[C:9]([C:10]=1[C:11]#[N:12])=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 450967232-methyl-5-nitro-1H-indole-3-carbonitrile

Product 1

HCID 1207821HCID 1207821, compound

Conditions

Temperature
80 °C

Procedure

2-methyl-5-nitro-1H-indole-3-carbonitrile (200 mg, 0.98 mmol) was dissolved in DMF (4 mL) followed by the addition of N,N-dimethylformamide dimethyl acetal (452 mg, 505 μL, 3.8 mmol). The mixture was heated at 80° C. for 0.5 h and turned from amber-colored to dark red over the course of the reaction. The solvent was removed in vacuo and 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-carbonitrile as a dark burgundy solid (235 mg, 89% yield) after drying. 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 C14H14N4O2=271.11; Found 271.07. 1H NMR (400 mHz, DMSO-d6) δ 8.12 (d, J=2.2 Hz, 1H), 7.99 (dd, J=9.0, 2.3 Hz, 1H), 7.72 (d, J=13.3 Hz, 1H), 7.61 (d, J=9.0 Hz, 1H), 5.17 (d, J=13.3 Hz, 1H), 3.73 (s, 3H), 3.00 (s, 6H).

Workup

  1. customover the course of the reaction
  2. customThe solvent was removed in vacuo
  3. washthe crude solid was washed with 5:1 EtOAc/hexane (6×10 mL)

Sources & evidence

ORD record
ord-bb9cef9501f944e1918e9fe275a716ab
Source dataset
uspto-grants-2008_12
Patent number
US07465738B2

Reaction notes

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