5-Bromo-7-chloroindoline → 3-(5-Bromo-7-chloro-2,3-dihydro-1H-indol-1-yl)-5-chloro-1-[(1R)-1-cyclopropylpropyl]-2(1H)-pyrazinone

HRID 1271183Notes

Reaction equation

HRID 1271183 reaction equation
[CH:1]1([C@H:4]([N:7]2[CH:12]=[C:11]([Cl:13])[N:10]=[C:9](Cl)[C:8]2=[O:15])[CH2:5][CH3:6])[CH2:3][CH2:2]1.[Br:16][C:17]1[CH:18]=[C:19]2[C:23](=[C:24]([Cl:26])[CH:25]=1)[NH:22][CH2:21][CH2:20]2>>[Br:16][C:17]1[CH:18]=[C:19]2[C:23](=[C:24]([Cl:26])[CH:25]=1)[N:22]([C:9]1[C:8](=[O:15])[N:7]([C@@H:4]([CH:1]3[CH2:3][CH2:2]3)[CH2:5][CH3:6])[CH:12]=[C:11]([Cl:13])[N:10]=1)[CH2:21][CH2:20]2

Participants

3

Reactant 2

HCID 167891645-Bromo-7-chloroindolineHCID 184527991-[(1R)-1-cyclopropylpropyl]-3,5-dichloro-2(1H)-pyrazinone

Product 1

HCID 101143213-(5-Bromo-7-chloro-2,3-dihydro-1H-indol-1-yl)-5-chloro-1-[(1R)-1-cyclopropylpropyl]-2(1H)-pyrazinone

Procedure

Prepared in a similar fashion as described for Example 413 using 1-[(1R)-1-cyclopropylpropyl]-3,5-dichloro-2(1H)-pyrazinone and 5-bromo-7-chloroindoline as the starting materials. mp 154–156° C.; 1H NMR (300 MHz, CDCl3) δ 7.31 (d, J=1.9 Hz, 1 H), 7.24 (d, J=1.8 Hz, 1 H), 7.01 (s, 1 H), 4.32 (t, J=8.1 Hz, 2 H), 4.05 (app. q, J=8.2 Hz, 1 H), 3.14 (t, J=7.9 Hz, 2 H), 1.96–1.83 (m, 2 H), 1.07–1.00 (m, 1 H), 0.94 (t, J=7.3 Hz, 3 H), 0.81–0.75 (m, 1 H), 0.55–0.48 (m, 2 H), 0.35–0.28 (m, 1 H); HRMS (ESI) calcd for C18H19N3OBrCl2 (M+H)+: 442.0089; Found m/z 442.0102.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-3cc7a2a10d094d03a9680a61e421220c
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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