Isovaleryl chloride → 2-(3-Chlorobenzoyl)-3-(isovalerylamino)-5-nitroindole

HRID 379787Notes

Reaction equation

[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[NH:4][C:3]=1[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=1.[C:23](Cl)(=[O:28])[CH2:24][CH:25]([CH3:27])[CH3:26]>>[Cl:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[C:14]([C:3]1[NH:4][C:5]2[C:10]([C:2]=1[NH:1][C:23](=[O:28])[CH2:24][CH:25]([CH3:27])[CH3:26])=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)=[O:22]

Participants

Reactant 2

HCID 66054Isovaleryl chloride

HCID 183679793-Amino-2-(3-chlorobenzoyl)-5-nitroindole

Product 1

HCID 183677662-(3-Chlorobenzoyl)-3-(isovalerylamino)-5-nitroindole

Procedure

The title compound was prepared according to the procedure described in Example 19 employing 3-amino-2-(3-chlorobenzoyl)-5-nitroindole (step 2) and isovaleryl chloride. m.p.: 197-199° C. 1H-NMR (CDCl3) δ: 9.91 (1H, br s), 9.37 (1H, d, J=2.2 Hz), 8.73 (1H, br.s), 8.24 (1H, dd, J=2.2, 9.2 Hz), 7.51-7.80 (4H, m), 7.38 (1H, d, J=9.2 Hz),2.37 (2H, br.s), 2.24-2.29 (1H, m), 1.07 (3H, s), 1.05 (3H, s)

Sources & evidence

ORD record: ord-007ca1f58fd84ec8a3d253878082c4a2
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300363B1

Reaction notes

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