Methyl vinyl ketone → HCID 86722449, compound

HRID 718842Notes

Reaction equation

HRID 718842 reaction equation
[Br:1][C:2]1[C:3]2[O:22][CH2:21][CH2:20][C:19]([OH:23])=[C:18]([C:24]#[N:25])[C:4]=2[CH:5]=[C:6]2[C:10]=1[N:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[N:8]=[CH:7]2.[CH:26]([C:28]([CH3:30])=[O:29])=[CH2:27]>COCCOC>[Br:1][C:2]1[C:3]2[O:22][CH2:21][CH2:20][C:19](=[O:23])[C:18]([CH2:27][CH2:26][C:28](=[O:29])[CH3:30])([C:24]#[N:25])[C:4]=2[CH:5]=[C:6]2[C:10]=1[N:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[N:8]=[CH:7]2

Participants

4

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 74221438HCID 74221438, compound

Product 1

HCID 86722449HCID 86722449, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

TEA (0.300 mL, 2.152 mmol) was added to a slurry of 10-bromo-1-(4-fluorophenyl)-6-hydroxy-7,8-dihydro-1H-oxepino[3,2-f]indazole-5-carbonitrile (102, R1=4-Fluorophenyl) (3.15 g, 7.87 mmol) in DME (40.0 mL) under a nitrogen atmosphere. Methyl vinyl ketone (1.30 mL, 15.8 mmol) was added dropwise. After about 47 h, the volatiles were removed under reduced pressure to afford 10-bromo-1-(4-fluorophenyl)-6-oxo-5-(3-oxobutyl)-5,6,7,8-tetrahydro-1H-oxepino[3,2-f]indazole-5-carbonitrile as a tan foam. LC/MS, method 3, Rt=2.33 min, MS m/z 470 and 472 (M+H)+. The material was dissolved in toluene (80 mL) in a 250 mL round bottom with Dean-Stark trap and reflux condenser attached under a nitrogen atmosphere. Toluene-4-sulfonic acid hydrate (0.599 g, 3.15 mmol) was added. After about 3 h at reflux, the mixture was allowed to cool to rt. Sat. aq. NaHCO3 (100 mL) was added.

Workup

  1. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-5c36ef7a30af45949d4d7526de07d812
Source dataset
uspto-grants-2015_11
Patent number
US09193744B2

Reaction notes

Loading…