Toluene → 2-Butyl-4-(2-methyl-1H-indol-3-yl)-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one

HRID 1013222Notes

Reaction equation

CC[N:3]([CH2:6][CH3:7])[CH2:4][CH3:5].[C:8]([OH:13])(=O)[C:9](O)=O.[CH2:14]([NH:18][NH2:19])[CH2:15][CH2:16][CH3:17].[C:20]1([CH3:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[Na+]>CCOC(C)=O>[CH2:14]([N:18]1[N:19]=[C:22]([C:21]2[C:5]3[C:4](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:3][C:6]=2[CH3:7])[CH:23]2[CH:9]([CH2:26][CH:20]=[CH:25][CH2:24]2)[C:8]1=[O:13])[CH2:15][CH2:16][CH3:17]

Participants

Conditions

Temperature: 70 °C

Procedure

The product of step a) (200 mg, 0.71 mmol) was treated with Et3N (0.71 mmol, 98 uL), n-butyl hydrazine oxalate (0.71 mmol, 126 mg) and 10 mL toluene. The suspension was refluxed for 48 h. The reaction was cooled, treated with 15 mL EtOAc and 5 mL 1M NaOH, and heated to 70° C. for 30 min. The organic layer was filtered through silica gel and further eluted with EtOAc. The combined eluent was concentrated to dryness to give the sub-titled compound which was used without further purification.

Workup

temperatureThe suspension was refluxed for 48 h
temperatureThe reaction was cooled
filtrationThe organic layer was filtered through silica gel
washfurther eluted with EtOAc
concentrationThe combined eluent was concentrated to dryness

Sources & evidence

ORD record: ord-271aa1c0033e4f35b85c87f2b750996e
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981912B2

Reaction notes

Loading…