HCID 20400411, compound → HCID 82493309, compound

HRID 2174518Notes

Reaction equation

HRID 2174518 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH3:14])=[CH:8]2)([CH3:3])[CH3:2].[CH2:15]([O:17]C1C=C2C(=CC=1)NC(C)=C2C=O)C>>[CH:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH3:14])=[C:8]2[CH:15]=[O:17])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 20400411HCID 20400411, compoundHCID 25219884HCID 25219884, compound

Product 1

HCID 82493309HCID 82493309, compound

Procedure

This compound was prepared from 408c (347 mg, 1.83 mmol) in a manner similar to that for 409a except for after the drop-wise addition of substituted indole, the solution was stirred for 90 min A cream-colored powder was obtained (313 mg, 78%): mp 179-181° C. TLC Rf 0.43 (75% EtOAc/hexanes). 1H NMR (600 MHz, d6-DMSO) δ 11.84 (s, 1H), 10.00 (s, 1H), 7.56 (d, 1H, J=2.4 Hz), 7.26-7.25 (d, 1H, J=8.64 Hz), 6.77-6.76 (dd, 1H, J1=8.7 Hz, J2=2.46 Hz), 4.56-4.50 (sep, 1H, J=6 Hz), 2.64 (s, 3H), 1.27-1.26 (d, 6H, J=6 Hz). 13C NMR (150 MHz, d6-DMSO) δ 184.0, 153.4, 148.6, 130.1, 126.4, 113.58, 113.56, 112.0, 105.5, 69.9, 22.0, 11.5. Elemental analysis calculated for C13H15NO2: C, 71.87; H, 6.96; N, 6.45. Found: C, 71.70; H, 6.83; N, 6.60.

Workup

  1. customwas obtained (313 mg, 78%)

Sources & evidence

ORD record
ord-1da9f4713a424399be67b25f930dcab2
Source dataset
uspto-grants-2015_06
Patent number
US09061994B1

Reaction notes

Loading…