Chloroacetaldehyde → 2-(5-methoxy-1-methyl-1H-indol-3-yl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine

HRID 1628040Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:22]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:16]2=[N:17][CH:18]=[C:19]([NH2:21])[N:20]=[C:15]2[CH:14]=1.Cl[CH2:32][CH:33]=O>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:22]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:29])([CH3:28])[CH3:30])[C:16]2[N:17]=[CH:18][C:19]3[N:20]([CH:32]=[CH:33][N:21]=3)[C:15]=2[CH:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In a round flask was added 6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-amine (0.065 g, 0.15 mmol) and 2-chloroacetaldehyde (˜50 wt % solution in water, 0.030 mL, 0.23 mmol) in EtOH (2 mL) and mixture was heated to about 80° C. for about 45 min. The mixture was concentrated under reduced pressure to give 2-(5-methoxy-1-methyl-1H-indol-3-yl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine (0.065 g, 95%): LC/MS (Table 2, b) Rt=1.79 min; MS m/z 448 (M+H)+.

Workup

concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-0bab2ec92de6429385620fda9530eca4
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785639B2

Reaction notes

Loading…