三乙胺 → methyl 5-chloro-4-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)nicotinate

HRID 20650

反应方程式

HRID 20650 反应方程式
[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]

参与物

8

反应物 4

HCID 8471三乙胺HCID 812191,3-双(二苯基膦)丙烷HCID 248494324-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-oneHCID 178418416HCID 178418416，化合物

产物 1

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

试剂、催化剂与溶剂 3

HCID 167845palladium acetate催化剂HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
80 °C

实验过程

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.

后处理

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

来源与证据

ORD记录
ord-fdf8967d91d349038d721fcbf25a7dc0
来源数据集
uspto-grants-2010_06
专利号
US07745646B2

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