m-Chloroperbenzoic acid → HCID 118666103, compound

HRID 630531Notes

Reaction equation

HRID 630531 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[N:10][C:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23](O)=[O:24])[CH:21]=3)[C:16]([S:26][CH3:27])=[CH:15]2)=[N:12][CH:13]=1.CN(C([O:35]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH:50]1[CH2:54][CH2:53][C@@H:52]([CH2:55][OH:56])[CH2:51]1.ClC1C=C(C=CC=1)C(OO)=O>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[N:10][C:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]([N:50]4[CH2:54][CH2:53][C@@H:52]([CH2:55][OH:56])[CH2:51]4)=[O:24])[CH:21]=3)[C:16]([S:26]([CH3:27])=[O:35])=[CH:15]2)=[N:12][CH:13]=1

Participants

5

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 7446913D-beta-ProlinolHCID 118666170HCID 118666170, compound

Product 1

HCID 118666103HCID 118666103, compound

Procedure

Prepared from 1-(5-(2-fluorophenyl)pyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylic acid in two reaction steps comprising a TBTU mediated amide coupling with (R)-pyrrolidin-3-ylmethanol (see also procedure 244c) and an oxidation utilizing m-chloroperoxybenzoic acid as oxidizing agent. Yellow solid. Yield: 0.12 g

Sources & evidence

ORD record
ord-7ecff4b297a045dfa1e62eb956b6681d
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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