5-Bromo-1-benzothiophene → HCID 58966965, compound

HRID 1948226Notes

Reaction equation

HRID 1948226 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH:12]=[C:11](B3OC(C)(C)C(C)(C)O3)[CH:10]=[CH:9][C:8]2=[O:22])=[C:4]([F:25])[CH:3]=1.Br[C:27]1[CH:35]=[CH:34][C:30]2[S:31][CH:32]=[CH:33][C:29]=2[CH:28]=1>>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:27]3[CH:35]=[CH:34][C:30]4[S:31][CH:32]=[CH:33][C:29]=4[CH:28]=3)[CH:10]=[CH:9][C:8]2=[O:22])=[C:4]([F:25])[CH:3]=1

Participants

3

Reactant 2

HCID 27765785-Bromo-1-benzothiopheneHCID 69349183HCID 69349183, compound

Product 1

HCID 58966965HCID 58966965, compoundYield 9%

Procedure

According to Scheme 17 Step 2: The title compound was prepared from 1-(4-chloro-2-fluorobenzyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one (1 eq, 1.26 mmol, 0.40 g) and 5-bromobenzo[b]thiophene (1.5 eq, 0.29 mmol, 0.06 g) according to the procedure described for Example 1 Step 2. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/AcOEt 90/10 and by crystallization with diisopropyl ether/pentane to afford the title compound (17 μmol, 6.4 mg, 9%) as a white solid.

Workup

  1. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2)
  2. customby crystallization with diisopropyl ether/pentane

Sources & evidence

ORD record
ord-c9613a59cc9c4d4fa2fa176b8d0a2f2b
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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