HCID 118108311, compound → HCID 118108337, compound

HRID 2174508Notes

Reaction equation

[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([CH3:15])=[C:9]2[CH:16]=O)[CH2:2][CH2:3][CH3:4].C(OC1C=C2C(=CC=1)NC(C)=C2/C=[CH:32]/[C:33]([C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1)=[O:34])C>>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([CH3:15])=[C:9]2/[CH:16]=[CH:32]/[C:33]([C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1)=[O:34])[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 118108311HCID 118108311, compound

HCID 118108312HCID 118108312, compound

Product 1

HCID 118108337HCID 118108337, compoundYield 57%

Procedure

5-Butoxy-2-methylindole-3-carboxaldehyde 409d (250 mg, 1.08 mmol) was reacted in a similar manner to that for 402a to yield a bright yellow powder (206 mg, 57%): mp 227-228° C. TLC Rf 0.33 (80% EtOAc/hexanes). 1H NMR (600 MHz, d6-DMSO) δ 11.39 (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=12.3 Hz), 7.34-7.31 (d, 1H, J=15.24 Hz), 7.30-7.28 (d, 1H, J=8.64 Hz), 6.84-6.82 (dd, 1H, J1=8.64 Hz, J2=2.34 Hz), 4.08-4.06 (t, 2H, J=6.48 Hz), 2.57 (s, 3H), 1.76-1.71 (m, 2H), 1.52-1.45 (m, 2H), 0.97-0.94 (t, 3H, J=7.38 Hz). 13C NMR (150 MHz, d6-DMSO) δ 188.2, 154.6, 150.6, 145.74, 145.19, 139.6, 131.0, 126.6, 121.4, 112.90, 112.25, 111.44, 109.3, 104.3, 64.8, 31.0, 18.9, 13.8, 12.2. Elemental analysis calculated for C21H22N2O2: C, 75.42; H, 6.63; N, 8.38. Found: C, 75.39; H, 6.55; N, 8.37.

Sources & evidence

ORD record: ord-7dec88505e0346b8aa4a6b23a8eefb71
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09061994B1

Reaction notes

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