Triethylamine → methyl 5-chloro-4-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)nicotinate

HRID 20650

반응식

HRID 20650 반응식
[C]=O.Br[C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:30])[C:9]=1[NH:10][C:11]1[C:20]2[C:15](=[C:16]([O:23][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[O:14][C:13](=[O:29])[CH:12]=1.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC)CC)C>CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C.CO>[Cl:30][C:8]1[CH:7]=[N:6][CH:5]=[C:4]([C:9]=1[NH:10][C:11]1[C:20]2[C:15](=[C:16]([O:23][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[O:14][C:13](=[O:29])[CH:12]=1)[C:13]([O:14][CH3:15])=[O:29]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 248494324-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-oneHCID 178418416HCID 178418416, 화합물

생성물 1

HCID 86618135methyl 5-chloro-4-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)nicotinate

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 887Methanol용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  1. temperatureto cool to rt
  2. filtrationThe mixture was filtered though Celite
  3. washwashed with EtOAc
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-fdf8967d91d349038d721fcbf25a7dc0
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745646B2

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