反応 #2201228

反応方程式

bromide

5-Bromo-3-oxazol-5-yl-1H-pyrrolo[2,3-b]pyridine

2-phenoxyphenylboronic acid

LiCl

Na2CO3

→

23

収率 46.2%

3-Oxazol-5-yl-5-(2-phenoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

収率 46.2%

溶媒

toluene

EtOH

反応条件

後処理

1. 1
   温度The reaction mixture was cooled
2. 2
   その他separated between brine (20 mL) and ethyl acetate (30 mL)
3. 3
   抽出The aqueous layer was extracted with ethyl acetate (2×30 mL)
4. 4
   乾燥The combined organic solutions were dried (MgSO4)
5. 5
   濃縮concentrated
6. 6
   その他The resulting solid was dry
7. 7
   workup.ADDITIONFractions containing the product
8. 8
   洗浄were eluted
9. 9
   その他to give a solid which
10. 10
    その他was triturated with ether

実験手順

A mixture of bromide 22 (300 mg, 1.14 mmol), 2-phenoxyphenylboronic acid (366 mg, 1.71 mmol), PdCl2(PPh3)2 (80.0 mg, 0.114 mmol), LiCl (145 mg, 3.42 mmol) and 1M Na2CO3 (2.85 mL, 2.82 mmol) in toluene (5.4 mL) and EtOH (5.4 mL) was refluxed overnight (105° C. oil bath temp.). The reaction mixture was cooled, and separated between brine (20 mL) and ethyl acetate (30 mL). The aqueous layer was extracted with ethyl acetate (2×30 mL). The combined organic solutions were dried (MgSO4) and concentrated. The resulting solid was dry loaded on a silicagel column. Fractions containing the product were eluted using ethyl acetate:hexane (1:1) (gradient elution) to give a solid which was triturated with ether to give 23 as a white solid (186 mg, 46%); 1H NMR (400 MHz, CDCl3) δ 6.94 (dd, J=8.8, 1.0 Hz, 2H), 7.05 (t, J=7.4 Hz, 1H), 7.08 (s, 1H), 7.12 (dd, J=8.1, 1.1 Hz, 1H), 7.33-7.20 (m, 3H), 7.38 (dt, J=9.2, 1.7 Hz, 1H), 7.56 (dd, J=7.6, 1.8 Hz, 1H), 7.64 (d, J=2.4 Hz, 1H), 7.85 (s, 1H), 8.32 (d, J=2.0 Hz, 1H), 8.59 (d, J=2.0 Hz, 1H), 9.35-9.20 (bs, NH).

出典