Isovaleryl chloride → HCID 18368086, compound

HRID 379864Notes

Reaction equation

[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:12]([C:14]1[CH:18]=[CH:17][O:16][CH:15]=1)=[O:13].[C:19](Cl)(=[O:24])[CH2:20][CH:21]([CH3:23])[CH3:22]>>[Cl:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([NH:1][C:19](=[O:24])[CH2:20][CH:21]([CH3:23])[CH3:22])=[C:3]([C:12]([C:14]3[CH:18]=[CH:17][O:16][CH:15]=3)=[O:13])[NH:4]2)=[CH:9][CH:8]=1

Participants

Reactant 2

HCID 66054Isovaleryl chloride

HCID 18368076HCID 18368076, compound

Product 1

HCID 18368086HCID 18368086, compound

Procedure

The title compound was prepared according to the procedure described in Ex. 19 from 3-amino-6-chloro-2-(3-furoyl)indole (Example 79) and isovaleryl chloride. m.p.: 202-203° C. (recrystallized from ethyl acetate) 1H-NMR (CDCl3) δ: 10.10 (1 H, br s), 8.28 (1 H, d, J=8.8 Hz), 8.23 (1 H, br s), 8.11 (1 H, dd, J=0.7, 1.5 Hz), 7.59 (1 H, dd, J=1.5, 1.8 Hz), 7.31 (1 H, d, J=1.8 Hz), 7.10 (1 H, dd, J=1.8, 8.8 Hz), 6.89 (1 H, dd, J=0.7, 1.8 Hz), 2.39-2.22 (3 H, m), 1.06 (6 H, d, J=6.6 Hz).

Workup

customm.p.: 202-203° C. (recrystallized from ethyl acetate) 1H-NMR (CDCl3) δ: 10.10 (1 H, br s), 8.28 (1 H, d, J=8.8 Hz), 8.23 (1 H, br s), 8.11 (1 H, dd, J=0.7, 1.5 Hz), 7.59 (1 H, dd, J=1.5, 1.8 Hz), 7.31 (1 H, d, J=1.8 Hz), 7.10 (1 H, dd, J=1.8, 8.8 Hz), 6.89 (1 H, dd, J=0.7, 1.8 Hz), 2.39-2.22 (3 H, m), 1.06 (6 H, d, J=6.6 Hz)

Sources & evidence

ORD record: ord-7ab491c788e04387be0460c156fd895f
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300363B1

Reaction notes

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