Aniline → HCID 24998228, compound

HRID 1910739Notes

Reaction equation

HRID 1910739 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[N:15]([C:16]=2[C:17](=[O:21])[C:18](Cl)=[O:19])[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:4][CH:3]=1.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[Cs+].[Cs+]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C=O)C.C1(C)C=CC=CC=1>[CH3:29][N:30]1[CH2:35][CH2:34][N:33]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]=[C:10]4[N:15]([C:16]=3[C:17](=[O:21])[C:18]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:19])[CH:14]=[CH:13][CH:12]=[CH:11]4)=[CH:4][CH:3]=2)[CH2:32][CH2:31]1

Participants

7

Reactant 4

HCID 6115AnilineHCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 86639584HCID 86639584, compound

Product 1

HCID 24998228HCID 24998228, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 21735183Dimethylformamide tolueneSolvent

Procedure

The starting material can be prepared from the compound of Reference Example 297, [2-(4-bromo-phenyl)-indolizin-3-yl]-oxo-acetyl chloride, and aniline. Step 1 describes a Buchwald reaction, e.g. with N-methylpiperazine, bis(triphenylphosphine) palladium(II) dichloride, cesium carbonate and DMF/toluene at 100° C.

Sources & evidence

ORD record
ord-3cd11c36e6a44ad081967ce61e4d2f60
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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