(4-Boc-Aminophenyl)Boronic Acid → HCID 69438746, compound

HRID 1948230Notes

Reaction equation

HRID 1948230 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH:12]=[C:11](Br)[CH:10]=[CH:9][C:8]2=[O:14])=[C:4]([F:17])[CH:3]=1.[C:18]([O:22][C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[C:8](=[O:14])[CH:9]=[CH:10][C:11]([C:29]3[CH:28]=[CH:27][C:26]([NH:25][C:23](=[O:24])[O:22][C:18]([CH3:20])([CH3:19])[CH3:21])=[CH:31][CH:30]=3)=[CH:12]2)=[C:4]([F:17])[CH:3]=1

Participants

3

Reactant 2

HCID 3613184(4-Boc-Aminophenyl)Boronic AcidHCID 69349998HCID 69349998, compound

Product 1

HCID 69438746HCID 69438746, compoundYield 75.1%

Procedure

According to Scheme 19 Step 1: The title compound was prepared from 1-(4-chloro-2-fluorobenzyl)-5-bromopyridin-2(1H)-one (1 eq, 2.81 mmol, 0.89 g, Example 1 Step 2) and 4-(tert-butoxycarbonyl)aminophenylboronic acid (1.5 eq, 4.20 mmol, 1.00 g) according to the procedure described for Example 1 Step 3. Reaction conditions: 2 hours at 80° C. The crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 50 g SiO2, CH2Cl2/AcOEt 90/10). The resulting brown solid washed twice with acetonitrile to afford tert-butyl 4-(1-(4-chloro-2-fluorobenzyl)-6-oxo-1,6-dihydropyridin-3-yl)phenylcarbamate (2.11 mmol, 0.90 g, 75%) as a beige solid.

Workup

  1. customReaction conditions
  2. custom2 hours
  3. customat 80° C
  4. customThe crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 50 g SiO2, CH2Cl2/AcOEt 90/10)
  5. washThe resulting brown solid washed twice with acetonitrile

Sources & evidence

ORD record
ord-2e33439ff684486990537eb7cb3a5849
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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