Butyryl chloride → 3-(Butyrylamino)-6-chloro-2-(3-methylbenzoyl)indole

HRID 379732Notes

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](=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1.[C:21](Cl)(=[O:25])[CH2:22][CH2:23][CH3:24]>>[C:21]([NH: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](=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1)(=[O:25])[CH2:22][CH2:23][CH3:24]

Participants

Reactant 2

HCID 8855Butyryl chloride

HCID 183678773-Amino-6-chloro-2-(3-methylbenzoyl)-1H-indole

Product 1

HCID 183677833-(Butyrylamino)-6-chloro-2-(3-methylbenzoyl)indole

Procedure

The title compound was prepared according to the procedure described in Example 19 employing 3-amino-6-chloro-2-(3-methylbenzoyl)indole (Example 21) and butyryl chloride. m.p.: 127-130° C. 1H-NMR (CDCl3) δ: 10.03 (1H, br s), 8.35-8.20 (2H, m), 7.62-7.54 (2H, m), 7.48-7.40 (2H, m), 7.28 (1H, d, J=1.8 Hz), 7.08 (1H, dd, J=1.8, 9.2 Hz), 2.55-2.35 (5H, m), 1.90-1.72 (2H, m), 1.04 (3H, t, J=7.3 Hz)

Sources & evidence

ORD record: ord-96df6576ae0f4fa495789a398ad0634c
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300363B1

Reaction notes

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