4-Bromoisoquinoline → HCID 11391278, compound

HRID 1948254Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.[C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)#[CH:13]>>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]#[C:13][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[N:4][CH:3]=2)=[CH:15][CH:16]=1

Participants

Reactant 2

HCID 737434-Bromoisoquinoline

HCID 2510201-Ethynyl-4-methoxybenzene

Product 1

HCID 11391278HCID 11391278, compoundYield 59%

Procedure

According to Scheme 29 Step 1: The title compound was prepared from 4-bromoisoquinoline (1 eq, 5.30 mmol, 1.10 g) and 1-ethynyl-4-methoxybenzene (1 eq, 5.30 mmol, 0.70 g) according to the procedure described for Example 13 Step 1. Reaction conditions: 70° C. for 4 hours. The crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column SiO2, cyclohexane/AcOEt 90/10 to 80/20) to afford 4-(2-(4-methoxyphenyl)ethynyl)isoquinoline (3.11 mmol, 0.81 g, 59%) as a white solid.

Workup

customReaction conditions
customThe crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column SiO2, cyclohexane/AcOEt 90/10 to 80/20)

Sources & evidence

ORD record: ord-6f966d89fd5f422d9ac28d1bf1a1fd55
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399493B2

Reaction notes

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