m-Chloroperbenzoic acid → N-(2-Amino-2-oxoethyl)-1-(5-(2-fluoro-5-methylphenyl)pyrimidin-2-yl)-N-methyl-3-(methylsulfinyl)-1H-indole-6-carboxamide

HRID 630522Notes

Reaction equation

HRID 630522 reaction equation
Br[C:2]1C=NC(N2C3C(=CC=C(C(OC)=O)C=3)C(SC)=C2)=NC=1.[NH2:23][C:24](=[O:57])[CH2:25][N:26]([CH3:56])[C:27]([C:29]1[CH:37]=[C:36]2[C:32]([C:33]([S:53]([CH3:55])=[O:54])=[CH:34][N:35]2[C:38]2[N:43]=[CH:42][C:41]([C:44]3[CH:49]=[C:48](OC)[CH:47]=[CH:46][C:45]=3[F:52])=[CH:40][N:39]=2)=[CH:31][CH:30]=1)=[O:28].C1C=C(Cl)C=C(C(OO)=O)C=1.Cl.CNCC(OC)=O.FC1C=CC(C)=CC=1C1C=NC(N2C3C(=CC=C(C(N(CC(OC)=O)C)=O)C=3)C(S(C)=O)=C2)=NC=1>>[NH2:23][C:24](=[O:57])[CH2:25][N:26]([CH3:56])[C:27]([C:29]1[CH:37]=[C:36]2[C:32]([C:33]([S:53]([CH3:55])=[O:54])=[CH:34][N:35]2[C:38]2[N:43]=[CH:42][C:41]([C:44]3[CH:49]=[C:48]([CH3:2])[CH:47]=[CH:46][C:45]=3[F:52])=[CH:40][N:39]=2)=[CH:31][CH:30]=1)=[O:28]

Participants

6

Reactant 5

HCID 70297m-Chloroperbenzoic acidHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 118666039Methyl 1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylateHCID 118666079N-(2-Amino-2-oxoethyl)-1-(5-(2-fluoro-5-methoxyphenyl)pyrimidin-2-yl)-N-methyl-3-(methylsulfinyl)-1H-indole-6-carboxamideHCID 118666202HCID 118666202, compound

Product 1

HCID 118671798N-(2-Amino-2-oxoethyl)-1-(5-(2-fluoro-5-methylphenyl)pyrimidin-2-yl)-N-methyl-3-(methylsulfinyl)-1H-indole-6-carboxamide

Procedure

Methyl 1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylate and 2-fluoro-5-methylyphenylboronic acid were submitted to a Suzuki reaction as described under 279b). The resulting coupling product was oxidized (m-CPBA) to the corresponding sulfoxide, transformed into its carboxylic acid (LiOH/THF/water) and then reacted with methyl 2-(methylamino)acetate hydrochloride (TBTU). Ester hydrolysis of the product methyl 2-(1-(5-(2-fluoro-5-methylphenyl)pyrimidin-2-yl)-N-methyl-3-(methylsulfinyl)-1H-indole-6-carboxamido)acetate, and subsequent reaction with HOBt ammonium salt provided the target compound as white solid. Yield: 0.13 g

Sources & evidence

ORD record
ord-e3e911e6165846daa4f5e0eb0b39e758
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

Loading…