Sodium Carbonate → ethyl 1-({3'-[3-[(cyclopropylamino)carbonyl]-4-oxo-1,8-naphthyridin-1(4H)-yl]biphenyl-4-yl}methyl)cyclobutanecarboxylate

HRID 1392722ノート

反応式

HRID 1392722 の反応式
[CH:1]1([NH:4][C:5]([C:7]2[C:16](=[O:17])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:18]3[CH:19]=[C:20]([C:24]4[CH:29]=[CH:28][C:27](C(O)=O)=[CH:26][CH:25]=4)[CH:21]=[CH:22][CH:23]=3)[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.BrC1C=CC([CH2:38][C:39]2([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:42][CH2:41][CH2:40]2)=CC=1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(O)CC.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:1]1([NH:4][C:5]([C:7]2[C:16](=[O:17])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:18]3[CH:19]=[C:20]([C:24]4[CH:25]=[CH:26][C:27]([CH2:38][C:39]5([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:42][CH2:41][CH2:40]5)=[CH:28][CH:29]=4)[CH:21]=[CH:22][CH:23]=3)[CH:8]=2)=[O:6])[CH2:3][CH2:2]1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 100254323'-[3-[(Cyclopropylamino)carbonyl]-4-oxo-1,8-naphthyridin-1(4H)-yl]-1,1'-biphenyl-4-carboxylic AcidHCID 69158278Ethyl 1-(4-bromobenzyl)cyclobutanecarboxylate

生成物 1

HCID 69158192ethyl 1-({3'-[3-[(cyclopropylamino)carbonyl]-4-oxo-1,8-naphthyridin-1(4H)-yl]biphenyl-4-yl}methyl)cyclobutanecarboxylate

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 86598119Dimethylformamide n-propanol溶媒

反応条件

温度
70 °C

実験手順

A mixture of NAPHTHYRIDNONE 3 (1.0 eq), ester from step 1 (1.5 eq), Na2CO3 (3.5eq; 2M in H2O), Pd(OAc)2 (0.05eq.) and PPh3 (0.15eq.) or PdCl2dppf (0.05 eq) in n-propanol-DMF (1:1, 0.1M) was stirred at 70° C. for 2 h. The mixture was cooled to rt, quenched with AcOH and diluted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (CH2Cl2/MeOH, 99:1) afforded the title compound.

後処理

  1. temperatureThe mixture was cooled to rt
  2. customquenched with AcOH
  3. additiondiluted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-eaaad3d4f83545049907e56012a1cf8a
出典データセット
uspto-grants-2008_03
特許番号
US07342024B2

反応ノート

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