5-Bromo-2-chloropyrimidine → (1-(5-Bromopyrimidin-2-yl)-3-(hydroxymethyl)-1H-indol-6-yl)(morpholino)methanone

HRID 630454Notes

Reaction equation

HRID 630454 reaction equation
[OH:1][CH2:2][C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[O:13])=[CH:9][CH:10]=2)[NH:5][CH:4]=1.[Br:20][C:21]1[CH:22]=[N:23][C:24](Cl)=[N:25][CH:26]=1.BrC1C=NC(N2C3C(=CC=C(C(N4CCOCC4)=O)C=3)C(SC)=C2)=NC=1>>[Br:20][C:21]1[CH:22]=[N:23][C:24]([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[C:8]([C:12]([N:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)=[O:13])[CH:7]=3)[C:3]([CH2:2][OH:1])=[CH:4]2)=[N:25][CH:26]=1

Participants

4

Reactant 3

HCID 6066655-Bromo-2-chloropyrimidineHCID 118666053(1-(5-Bromopyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(morpholino)methanoneHCID 118666232(3-(Hydroxymethyl)-1H-indol-6-yl)(morpholino)methanone

Product 1

HCID 118666263(1-(5-Bromopyrimidin-2-yl)-3-(hydroxymethyl)-1H-indol-6-yl)(morpholino)methanone

Procedure

Prepared from 27b) (700 mg, 2.69 mmol, 1.0 eq) and 5-bromo-2-chloropyrimidine (520 mg, 2.69 mmol, 1.0 eq) in an analogous manner to the procedure of 1c). The raw product was purified by column chromatography [100-200 mesh; ethyl acetate/petrolether=7:3]. White solid. Yield: 400 mg (35% of theory).

Workup

  1. customThe raw product was purified by column chromatography [100-200 mesh; ethyl acetate/petrolether=7:3]

Sources & evidence

ORD record
ord-c85194d36f0f48fa954d55ccfe24f875
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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