5-Bromo-7-chloroindoline → HCID 10296369, compound

HRID 1271181Notes

Reaction equation

HRID 1271181 reaction equation
Cl[C:2]1[C:3](=[O:14])[N:4]([CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH:5]=[C:6]([Cl:8])[N:7]=1.[Br:15][C:16]1[CH:17]=[C:18]2[C:22](=[C:23]([Cl:25])[CH:24]=1)[NH:21][CH2:20][CH2:19]2>>[Br:15][C:16]1[CH:17]=[C:18]2[C:22](=[C:23]([Cl:25])[CH:24]=1)[N:21]([C:2]1[C:3](=[O:14])[N:4]([CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH:5]=[C:6]([Cl:8])[N:7]=1)[CH2:20][CH2:19]2

Participants

3

Reactant 2

HCID 167891645-Bromo-7-chloroindolineHCID 220043393,5-dichloro-1-(1-ethylpropyl)-2(1H)-pyrazinone

Product 1

HCID 10296369HCID 10296369, compound

Procedure

Prepared in a similar fashion as described for Example 413 using 3,5-dichloro-1-(1-ethylpropyl)-2(1H)-pyrazinone and 5-bromo-7-chloroindoline as the starting materials. mp 156–157° C.; 1H NMR (300 MHz, CDCl3): δ 7.25 (d, J=1.8 Hz, 1 H), 7.19 (d, J=2.9 Hz, 1 H), 6.71 (s, 1 H), 4.75–4.69 (m, 1 H), 4.27 (t, J=7.9 Hz, 2 H), 3.07 (t, J=8.1 Hz, 2 H), 1.78–1.51 (m, 4 H), 0.81 (t, J=7.3 Hz, 6 H); HRMS (ESI) calcd for C17H19N3OBrCl2 (M+H)+: 430.0089; Found m/z 430.0106.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-4038102005a64b45b747c4eba65033c7
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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