تفاعل #57569

معادلة التفاعل

product

3-methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid ethyl ester

3-methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid ethyl ester

methane sulfonamide

biphenyl-2-yl-di-tert-butyl-phosphane

potassium phosphate

→

4-methanesulfonylamino-3-methyl-benzofuran-2-carboxylic acid ethyl ester

المردود 67.0%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe resulting mixture was heated
2. 2
   درجة الحرارةat reflux for 3 h

الإجراء التجريبي

To the product of Example 20, Step 1, 3-methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid ethyl ester (800 mg, 2.27 mmol), in 25 mL of toluene were added methane sulfonamide (650 mg, 6.82 mmol, 3 eq), Pd2 (dba)3 (208 mg, 0.23 mmol, 0.1 eq), biphenyl-2-yl-di-tert-butyl-phosphane (68 mg, 0.23 mmol, 0.1 eq), and tribasic potassium phosphate (965 mg, 4.55 mmol, 2 eq) under nitrogen and the resulting mixture was heated at reflux for 3 h. After work up and trituration, 4-methanesulfonylamino-3-methyl-benzofuran-2-carboxylic acid ethyl ester was obtained in 67% yield (450 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.3 (t, J=7.1 Hz, 3 H) 2.7 (s, 3 H) 3.1 (s, 3 H) 4.4 (q, J=7.1 Hz, 2 H) 7.3 (dd, J=7.7, 0.9 Hz, 1 H) 7.5 (dd, J=8.3, 7.6 Hz, 1 H) 7.6 (m, 1 H) 9.5 (s, 1 H).

المصدر