2-Methoxyphenylboronic acid → HCID 86703182, compound

HRID 2204378Notes

Reaction equation

HRID 2204378 reaction equation
Br[C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[C:5]2[CH:10]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[CH3:27])[N:11]([CH:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:12](=[O:13])[C:4]=2[CH:3]=1.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O.BrC1N(C(C)C)C2C(C3C=CC(Cl)=CC=3)N(C3C=C(Cl)C=CC=3C)C(=O)C=2C=1.C(C1C=CC(OC)=C(B(O)O)C=1)#N>>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([CH:10]2[C:5]3[N:6]([CH:7]([CH3:9])[CH3:8])[C:2]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[O:29][CH3:28])=[CH:3][C:4]=3[C:12](=[O:13])[N:11]2[CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[C:21]([CH3:27])[CH:22]=1

Participants

5

Reactant 4

HCID 27339582-Methoxyphenylboronic acidHCID 23005336(5-Cyano-2-Methoxyphenyl)Boronic AcidHCID 867031692-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-oneHCID 86703183HCID 86703183, compound

Product 1

HCID 86703182HCID 86703182, compound

Procedure

The title compound was prepared in analogy to the procedure described for Example 17 but 2-bromo-6-(4-chloro-2-methyl-phenyl)-1-isopropyl-5-(tetrahydro-pyran-4-yl)-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one (Intermediate AK) and 2-methoxyphenylboronic acid were used instead of 2-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one and 5-cyano-2-methoxyphenylboronic acid respectively. The title compound was obtained as a white solid. tR: 7.52 min (HPLC 2); ESI-MS: tR=1.25 min, [M+H]+479/481 (LC-MS 1); TLC: Rf=0.36 (EtOAc).

Workup

  1. customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record
ord-bf300c79c48b4612b41dccbfa3497887
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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