Lithium Hydroxide → (1-(5-(2-Fluoro-5-methylphenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(pyrrolidin-1-yl)methanone

HRID 630513Notes

Reaction equation

HRID 630513 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](OC)=[O:18])[CH:15]=3)[C:10]([S:21][CH3:22])=[CH:9]2)=[N:6][CH:7]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=1B(O)O.ClC1C=C(C=CC=1)C(OO)=[O:39].[OH-].[Li+].CN(C(ON1N=NC2[CH:58]=[CH:59][CH:60]=[N:61][C:56]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCC1>>[F:23][C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=1[C:2]1[CH:7]=[N:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([N:61]4[CH2:60][CH2:59][CH2:58][CH2:56]4)=[O:18])[CH:15]=3)[C:10]([S:21]([CH3:22])=[O:39])=[CH:9]2)=[N:4][CH:3]=1

Participants

7

Reactant 6

HCID 3939Lithium HydroxideHCID 31268PyrrolidineHCID 70297m-Chloroperbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 103518842-Fluoro-5-methylbenzeneboronic acidHCID 118666039Methyl 1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylate

Product 1

HCID 118666234(1-(5-(2-Fluoro-5-methylphenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(pyrrolidin-1-yl)methanone

Procedure

The synthesis example was prepared from methyl 1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylate in four chemical steps comprising a Suzuki reaction with (2-fluoro-5-methylphenyl)boronic acid, an oxidation with m-chloroperoxybenzoic acid, a hydrolysis of the methyl ester under use of lithium hydroxide and finally an amidation with HATU as coupling reagent and pyrrolidine as amine. White solid. Yield: 0.08 g

Sources & evidence

ORD record
ord-f64d2dcaacc344c191a72ee4dfa9485d
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

Loading…