2-Methoxyphenylboronic acid → HCID 86703178, compound

HRID 2204376Notes

Reaction equation

HRID 2204376 reaction equation
Br[C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[C:5]2[CH:10]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[N:11]([C:14]3[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:15]=3[C:16]#[N:17])[C:12](=[O:13])[C:4]=2[CH:3]=1.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=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:22][C:20]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([N:11]2[C:12](=[O:13])[C:4]3[CH:3]=[C:2]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[O:31][CH3:30])[N:6]([CH:7]([CH3:9])[CH3:8])[C:5]=3[CH:10]2[C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)[CH:21]=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 86703179HCID 86703179, compound

Product 1

HCID 86703178HCID 86703178, compound

Procedure

The title compound was prepared in analogy to the procedure described for Example 17 but 2-[2-bromo-6-(4-chloro-phenyl)-1-isopropyl-4-oxo-4,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-5-yl]-4-chloro-benzonitrile (Intermediate AB) 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 light brown solid. tR: 7.83 min (HPLC 2); ESI-MS: tR=1.32 min, [M+H]+ 516/518 (LC-MS 1); TLC: Rf=0.26 (1:4 EtOAc/hexanes).

Workup

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

Sources & evidence

ORD record
ord-ad981105e30240b2b9c3321e00868abe
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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