Boron trifluoride etherate → HCID 58914677, compound

HRID 1297767Notes

Reaction equation

[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](O)([C:14]2[CH:19]=[C:18]([CH3:20])[C:17]([O:21][CH3:22])=[C:16]([CH3:23])[CH:15]=2)[C:6]1=[O:25].C([SiH](CC)CC)C.B(F)(F)F.CCOCC>ClC(Cl)C>[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]([C:14]2[CH:19]=[C:18]([CH3:20])[C:17]([O:21][CH3:22])=[C:16]([CH3:23])[CH:15]=2)[C:6]1=[O:25]

Participants

Conditions

Temperature: 50 °C

Procedure

Dissolve 1-(2-chloro-benzyl)-3-hydroxy-3-(4-methoxy-3,5-dimethyl-phenyl)-1,3-dihydro-indol-2-one (430 mg, 1.05 mmol) in dichloroethane (15 mL) and treat with triethylsilane (0.503 mL, 3.15 mmol) and boron trifluoride diethyl etherate (0.038 mL, 0.3 mmol) under nitrogen. Heat at 50° C. for 24 h. Add more triethyl silane (0.250 mL, 1.57 mmol) and boron trifluoride diethyl etherate (0.030 mL, 0.24 mmol) and continue for 6 h. at which time reaction complete. Concentrate in vacuo and purify by flash chromatography (gradient of 5% EtOAc/hexanes to 25% EtOAc/hexanes) to obtain 319 mg (78%) of the title compound as a white solid. MS (ES): m/z=392 (M+1), 390 (M−1); 1H NMR(DMSO-d6): δ7.54 (m, 1H), 7.36-7.29 (m, 2H), 7.25 (t, J=7.9, 7.6 Hz, 1H), 7.18-7.13 (m, 2H), 7.03 (t, J=7.4 Hz, 1H), 6.88 (d, J=7.9 Hz, 1H), 6.85 (s, 2H), 5.02 (s, 2H), 4.90 (s, 1H), 3.65 (s, 3H), 2.20 (s, 6H).

Workup

customcontinue for 6 h. at which time reaction complete
concentrationConcentrate in vacuo
custompurify by flash chromatography (gradient of 5% EtOAc/hexanes to 25% EtOAc/hexanes)

Sources & evidence

ORD record: ord-0cbe121dd61343549997a17961615d77
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250442B2

Reaction notes

Loading…