HCID 100304374, compound → HCID 118108318, compound

HRID 2174507Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=O)=[CH:8][C:7]([O:13][CH2:14][CH2:15][CH3:16])=[CH:6][CH:5]=2.C(OC1C=C2C(=CC=1)NC(C)=C2/C=[CH:31]/[C:32]([C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1)=[O:33])C>>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1/[CH:11]=[CH:31]/[C:32]([C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1)=[O:33])=[CH:8][C:7]([O:13][CH2:14][CH2:15][CH3:16])=[CH:6][CH:5]=2

Participants

Reactant 2

HCID 100304374HCID 100304374, compound

HCID 118108311HCID 118108311, compound

Product 1

HCID 118108318HCID 118108318, compoundYield 69%

Procedure

2-Methyl-5-propoxyindole-3-carboxaldehyde 409b (200 mg, 0.920 mmol) was reacted in a similar manner to that for 402a to yield a bright yellow powder (204 mg, 69%): mp 228-229° C. TLC Rf 0.40 (80% EtOAc/hexanes). 1H NMR (600 MHz, d6-DMSO) δ 11.88 (s, 1H), 8.81-8.80 (m, 2H), 8.08-8.06 (d, 1H, J=15.3 Hz), 7.93-7.92 (m, 2H), 7.41 (d, 1H, J=2.22 Hz), 7.34-7.31 (d, 1H, J=15.24 Hz), 7.30-7.29 (d, 1H, J=8.64 Hz), 6.85-6.83 (dd, 1H, J1=8.64 Hz, J2=2.28 Hz), 4.04-4.02 (t, 2H, 6.54 Hz), 2.56 (s, 3H), 1.80-1.74 (sex, 2H, J=6.66 Hz), 1.03-1.01 (t, 3H, J=7.38 Hz). 13C NMR (150 MHz, d6-DMSO) δ 188.2, 154.6, 150.6, 145.75, 145.18, 139.6, 131.0, 126.6, 121.4, 112.90, 112.25, 111.4, 109.3, 104.4, 69.6, 22.3, 12.2, 10.6. Elemental analysis calculated for C20H20N2O2: C, 74.98; H, 6.29; N, 8.74. Found: C, 75.00; H, 6.23; N, 8.69.

Sources & evidence

ORD record: ord-e6aa2bf10f9447b0b8507fac91a18f44
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09061994B1

Reaction notes

Loading…