2-Bromo-3-methoxypyridine → HCID 72205350, compound

HRID 2204385Notes

Reaction equation

Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:45])=[C:15]([N:17]2[C:24](=[O:25])[C:23]3[CH:22]=[C:21](B4OC(C)(C)C(C)(C)O4)[N:20]([CH:35]([CH3:37])[CH3:36])[C:19]=3[CH:18]2[C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=2)[CH:16]=1.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:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:45])=[C:15]([N:17]2[C:24](=[O:25])[C:23]3[CH:22]=[C:21]([C:2]4[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=4)[N:20]([CH:35]([CH3:37])[CH3:36])[C:19]=3[CH:18]2[C:38]2[CH:39]=[CH:40][C:41]([Cl:44])=[CH:42][CH:43]=2)[CH:16]=1

Participants

Reactant 4

HCID 903642-Bromo-3-methoxypyridine

HCID 23005336(5-Cyano-2-Methoxyphenyl)Boronic Acid

HCID 867031692-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

HCID 86703194HCID 86703194, compound

Product 1

HCID 72205350HCID 72205350, compound

Procedure

The title compound was prepared in analogy to the procedure described for Example 17 but 2-bromo-3-methoxy-pyridine [24100-18-3] and 5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one (Step 113.1) 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: 6.54 min (HPLC 2); ESI-MS: tR=1.27 min, [M+H]+ 506/508/510 (LC-MS 1); TLC: Rf=0.21 (98:2 CH2Cl2/MeOH).

Workup

customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record: ord-6bb1626a076c4aaca55113c1a48d9b40
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365576B2

Reaction notes

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