تفاعل #2359424

معادلة التفاعل

5-bromo-2-fluoro-6-methyl-benzofuran

2-aminopyridine-5-boronic acid pinacol ester

N-(5-(2,2-difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)pyrazin-2-yl)-2-fluorobenzamide

K3PO4

EA

→

5-(2-fluoro-6-methylbenzo[b]furan-5-yl)-2-pyridylamine

المردود 56.8%

المذيبات

ACN

dioxane

H2O

ظروف التفاعل

المعالجة

1. 1
   أخرىwas bubbled with argon
2. 2
   درجة الحرارةAfter cooling down to r.t.
3. 3
   غسيلwashed with aq. NaHCO3 and brine
4. 4
   تجفيفphase was dried over Na2SO4
5. 5
   تركيزconcentrated

الإجراء التجريبي

A mixture of 5-bromo-2-fluoro-6-methyl-benzofuran (230) (78.5 mg, 0.34 mmol), 2-aminopyridine-5-boronic acid pinacol ester (11) (151 mg, 2 eq), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (48 mg, 10% mol) and K3PO4 (145 mg, 0.69 mmol) in 2 ml ACN, 2 ml dioxane, 0.5 ml H2O was bubbled with argon before heated at 85° C. for 3 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine. Org. phase was dried over Na2SO4, concentrated and then subjected to silica gel flash column chromatography (0-100% B, A: hexane; B: EA) to give 5-(2-fluoro-6-methylbenzo[b]furan-5-yl)-2-pyridylamine (231) (46.8 mg, purity>95%, yield: 56.8%) as yellow solid.

المصدر