Sodium Carbonate → 5-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-4-(4-formyl-phenyl)-isoxazole-3-carboxylic acid ethylamide

HRID 1891188ノート

反応式

HRID 1891188 の反応式
[CH2:1]([NH:3][C:4]([C:6]1[C:10](I)=[C:9]([C:12]2[CH:17]=[C:16]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:15]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:14][C:13]=2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:8][N:7]=1)=[O:5])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].[CH:44]([C:46]1[CH:51]=[CH:50][C:49](B(O)O)=[CH:48][CH:47]=1)=[O:45]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([NH:3][C:4]([C:6]1[C:10]([C:49]2[CH:50]=[CH:51][C:46]([CH:44]=[O:45])=[CH:47][CH:48]=2)=[C:9]([C:12]2[CH:17]=[C:16]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:15]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:14][C:13]=2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:8][N:7]=1)=[O:5])[CH3:2]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 24773447HCID 24773447、化合物

生成物 1

HCID 247735315-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-4-(4-formyl-phenyl)-isoxazole-3-carboxylic acid ethylamide

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

5-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-4-iodo-isoxazole-3-carboxylic acid ethylamide (1 eq) was dissolved in DMF and 1M Na2CO3 (aq) (3 eq) was added, followed by 4-formylphenylboronic acid (2 eq) and catalytic PdCl2(PPh3)2. Nitrogen was bubbled through the solution for ten minutes at ambient temperature, after which time, the temperature was elevated to 80° C. under a nitrogen atmosphere, for 2 hours. The reaction mixture was allowed to cool to room temperature and the reaction mixture was diluted with ethyl acetate. This solution was washed with brine, then dried over magnesium sulfate, filtered and concentrated in vacuo to give an oil which was purified by column chromatography, eluting with 10% EtOAc in hexane, to give 5-(2,4-bis-benzyloxy-5-isobutyl-phenyl)-4-(4-formyl-phenyl)-isoxazole-3-carboxylic acid ethylamide as a white solid.

後処理

  1. customNitrogen was bubbled through the solution for ten minutes at ambient temperature
  2. additionthe reaction mixture was diluted with ethyl acetate
  3. washThis solution was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give an oil which
  8. customwas purified by column chromatography
  9. washeluting with 10% EtOAc in hexane

出典と根拠

ORDレコード
ord-f7e04c89db904afab982f983c936233d
出典データセット
uspto-grants-2013_08
特許番号
US08507480B2

反応ノート

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