تفاعل #48928

ord-fdf8967d91d349038d721fcbf25a7dc0

معادلة التفاعل

[C]=O
Carbon monoxide
COc1ccc2c(Nc3c(Cl)cncc3Br)cc(=O)oc2c1OC1CCCC1
4-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one
c1ccc(P(CCCP(c2ccccc2)c2ccccc2)c2ccccc2)cc1
DPPP
CCN(CC)CC
triethylamine
COC(=O)c1cncc(Cl)c1Nc1cc(=O)oc2c(OC3CCCC3)c(OC)ccc12
methyl 5-chloro-4-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)nicotinate

المذيبات

ظروف التفاعل

درجة الحرارة
80°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةto cool to rt
  2. 2
    ترشيحThe mixture was filtered though Celite
  3. 3
    غسيلwashed with EtOAc
  4. 4
    تركيزconcentrated

الإجراء التجريبي

Carbon monoxide was bubbled through a mixture of 4-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (0.240 g, 0.514 mmol, Example 11), Pd(OAc)2 (11 mg, 0.051 mmol), DPPP (21 mg, 0.051 mmol), triethylamine (0.22 mL, 1.5 mmol), methanol (1 mL), and anhydrous DMF (4 mL). The reaction was heated at 80° C. for 2 d under an atmosphere of CO and then allowed to cool to rt. The mixture was filtered though Celite, washed with EtOAc, and concentrated to give methyl 5-chloro-4-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)nicotinate.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07745646B2uspto-grants-2010_06