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

HRID 1271187Notes

Reaction equation

HRID 1271187 reaction equation
Br[C:2]1[C:3](=[O:15])[N:4]([C@@H:9]([CH2:12][O:13][CH3:14])[CH2:10][CH3:11])[CH:5]=[C:6]([Br:8])[N:7]=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:8][C:6]1[N:7]=[C:2]([N:22]2[C:23]3[C:19](=[CH:18][C:17]([Br:16])=[CH:25][C:24]=3[Cl:26])[CH2:20][CH2:21]2)[C:3](=[O:15])[N:4]([C@@H:9]([CH2:12][O:13][CH3:14])[CH2:10][CH3:11])[CH:5]=1

Participants

3

Reactant 2

HCID 167891645-Bromo-7-chloroindolineHCID 692205703,5-dibromo-1-[(1R)-1-(methoxymethyl)propyl]2(1H)-pyrazinone

Product 1

HCID 101635215-Bromo-3-(5-bromo-7-chloro-2,3-dihydro-1H-indol-1-yl)-1-[(1R)-1-(methoxymethyl)propyl]-2(1H)-pyrazinone

Procedure

Prepared in a similar fashion as described for Example 413 using 3,5-dibromo-1-[(1R)-1-(methoxymethyl)propyl]-2(1H)-pyrazinone and 5-bromo-7-chloroindoline as the starting materials. mp 118° C.; 1H NMR (300 MHz, CDCl3): δ 7.31 (s, 1 H), 7.24 (s, 1 H), 7.13 (s, 1 H), 4.98–4.90 (m, 1 H), 4.32 (t, J=7.9 Hz, 2 H), 3.66 (dd, J=10.7, 5.9 Hz, 1 H), 3.55 (dd, J=10.6, 3.3 Hz, 1 H), 3.35 (s, 3 H), 3.13 (t, J=7.9 Hz, 2 H), 1.85–1.74 (m, 2 H), 0.93 (t, J=7.3 Hz, 3 H); HRMS (ESI) calcd for C17H19N3O2Br2Cl (M+H)+: 489.0543; Found m/z 489.9534.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-38ffb9f753c6469e899ddbd743112bf3
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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