Triacetoxyperiodinane → (1-(5-(5-Ethoxy-2-fluorophenyl)pyrimidin-2-yl)-3-(1-hydroxyethyl)-1H-indol-6-yl)(morpholino)methanone

HRID 630538

Reaction equation

HRID 630538 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[O:18])[CH:15]=3)[C:10]([CH2:25][OH:26])=[CH:9]2)=[N:6][CH:7]=1.[CH2:27]([O:29][C:30]1[CH:31]=[CH:32][C:33]([F:39])=[C:34](B(O)O)[CH:35]=1)[CH3:28].[CH3:40]C(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C[Mg]Br>>[CH2:27]([O:29][C:30]1[CH:31]=[CH:32][C:33]([F:39])=[C:34]([C:2]2[CH:3]=[N:4][C:5]([N:8]3[C:16]4[C:11](=[CH:12][CH:13]=[C:14]([C:17]([N:19]5[CH2:24][CH2:23][O:22][CH2:21][CH2:20]5)=[O:18])[CH:15]=4)[C:10]([CH:25]([OH:26])[CH3:40])=[CH:9]3)=[N:6][CH:7]=2)[CH:35]=1)[CH3:28]

Participants

5

Reactant 4

HCID 159087TriacetoxyperiodinaneHCID 162174685-Ethoxy-2-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 118666263(1-(5-Bromopyrimidin-2-yl)-3-(hydroxymethyl)-1H-indol-6-yl)(morpholino)methanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 118671990(1-(5-(5-Ethoxy-2-fluorophenyl)pyrimidin-2-yl)-3-(1-hydroxyethyl)-1H-indol-6-yl)(morpholino)methanone

Procedure

The target compound was prepared from intermediate 27c in three reaction steps comprising a Suzuki reaction with (5-ethoxy-2-fluorophenyl)boronic acid, an oxidation with Dess-Martin periodinane and a Grignard reaction with methylmagnesium bromide. White solid. Yield: 110 mg

Sources & evidence

ORD record
ord-05bb3ba7f9024c3287587a71a85b346e
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Linked notes

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