HCID 18452815, compound → 5-Bromo-1-(1-ethylpropyl)-3-(5-methoxy-7-methyl-2,3-dihydro-1H-indol-1-yl)-2(1H)-pyrazinone

HRID 2251011Notes

Reaction equation

HRID 2251011 reaction equation
Br[C:2]1[C:3](=[O:14])[N:4]([CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH:5]=[C:6]([Br:8])[N:7]=1.Cl.[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:24](=[C:25]([CH3:27])[CH:26]=1)[NH:23][CH2:22][CH2:21]2>>[Br:8][C:6]1[N:7]=[C:2]([N:23]2[C:24]3[C:20](=[CH:19][C:18]([O:17][CH3:16])=[CH:26][C:25]=3[CH3:27])[CH2:21][CH2:22]2)[C:3](=[O:14])[N:4]([CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH:5]=1

Participants

3

Reactant 2

HCID 18452815HCID 18452815, compoundHCID 220043223,5-dibromo-1-(1-ethylpropyl)-2(1H)-pyrazinone

Product 1

HCID 102229905-Bromo-1-(1-ethylpropyl)-3-(5-methoxy-7-methyl-2,3-dihydro-1H-indol-1-yl)-2(1H)-pyrazinone

Procedure

Prepared in a similar fashion as described for Example 413 using 3,5-dibromo-1-(1-ethylpropyl)-2(1H)-pyrazinone and 5-methoxy-7-methylindoline hydrochloride as the starting materials. mp 152-154° C.; 1H NMR (300 MHz, CDCl3): δ 6.73 (s, 1 H), 6.67 (s, 1 H), 6.59 (d, J=1.9 Hz, 1 H), 4.84-4.76 (m, 1 H), 4.38 (t, J=7.7 Hz, 2 H), 3.78 (s, 3 H), 3.05 (t, J=7.7 Hz, 2 H), 2.06 (s, 3 H), 1.87-1.73 (m, 2 H), 1.70-1.59 (m, 2 H), 0.89 (t, J=7.3 Hz, 6H); HRMS (ESI) calcd for C19H25N3O2Br (M+H)+: 406.1130; found m/z 406.1125.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-b7349177785b40c48c0b79416b727d16
Source dataset
uspto-grants-2008_01
Patent number
US07319100B2

Reaction notes

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