HCID 15157644, compound → HCID 100304374, compound

HRID 2174517Notes

Reaction equation

HRID 2174517 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([O:11][CH2:12][CH2:13][CH3:14])=[CH:6][CH:5]=2.[CH2:15]([O:17]C1C=C2C(=CC=1)NC(C)=C2C=O)C>>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:15]=[O:17])=[CH:8][C:7]([O:11][CH2:12][CH2:13][CH3:14])=[CH:6][CH:5]=2

Participants

3

Reactant 2

HCID 15157644HCID 15157644, compoundHCID 20400411HCID 20400411, compound

Product 1

HCID 100304374HCID 100304374, compound

Procedure

This compound was prepared from 408b (263 mg, 1.39 mmol) in a manner similar to that for 409a except for after the drop-wise addition of substituted indole, the solution was stirred for 1 h. A cream-colored powder was obtained (228 mg, 75%): mp 156-158° C. TLC Rf 0.52 (75% EtOAc/hexanes). 1H NMR (600 MHz, d6-DMSO) δ 11.85 (s, 1H), 10.00 (s, 1H), 7.55 (d, 1H, J=2.46 Hz), 7.27-7.25 (d, 1H, J=8.7 Hz), 6.79-6.77 (dd, 1H, J1=8.7 Hz, J2=2.52 Hz), 3.92-3.90 (t, 2H, J=6.54 Hz), 2.64 (s, 3H), 1.77-1.71 (sex, 2H, J=7.38 Hz), 1.00-0.98 (t, 3H, J=7.38 Hz). NMR (150 MHz, d6-DMSO) δ 184.0, 154.9, 148.5, 130.0, 126.4, 113.6, 112.26, 112.04, 103.2, 69.3, 22.2, 11.5, 10.5. Elemental analysis calculated for C13H15NO2: C, 71.87; H, 6.96; N, 6.45. Found: C, 71.74; H, 6.81; N, 6.42.

Workup

  1. customA cream-colored powder was obtained (228 mg, 75%)

Sources & evidence

ORD record
ord-bf66b5f1fbc847b18c2583c8835ba798
Source dataset
uspto-grants-2015_06
Patent number
US09061994B1

Reaction notes

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