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Sodium Bicarbonate → 1,1-dimethylethyl 4-(6-{5-[(ethylamino)carbonyl]-3-fluoro-2-methylphenyl}-1H-indazol-3-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate

HRID 2246626
ノート
印刷プレビュー

反応式

HRID 2246626 の反応式
[CH2:1]([NH:3][C:4](=[O:23])[C:5]1[CH:10]=[C:9]([C:11]2[CH:19]=[C:18]3[C:14]([C:15](I)=[N:16][NH:17]3)=[CH:13][CH:12]=2)[C:8]([CH3:21])=[C:7]([F:22])[CH:6]=1)[CH3:2].CC1(C)C(C)(C)OB([C:32]2[CH2:33][CH2:34][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:36][CH:37]=2)O1.C(=O)([O-])O.[Na+]>C(O)(C)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([NH:3][C:4]([C:5]1[CH:6]=[C:7]([F:22])[C:8]([CH3:21])=[C:9]([C:11]2[CH:19]=[C:18]3[C:14]([C:15]([C:32]4[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH:33]=4)=[N:16][NH:17]3)=[CH:13][CH:12]=2)[CH:10]=1)=[O:23])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 178464894HCID 178464894、化合物2 回

生成物 1

HCID 588996041,1-dimethylethyl 4-(6-{5-[(ethylamino)carbonyl]-3-fluoro-2-methylphenyl}-1H-indazol-3-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate収率 66.5%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 3776Isopropanol溶媒

反応条件

温度
150 °C

実験手順

A mixture of N-ethyl-3-fluoro-5-(3-iodo-1H-indazol-6-yl)-4-methylbenzamide (Intermediate 19, 2.34 g), 1,1-dimethylethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate (1.71 g), aqueous sodium hydrogen carbonate (1M, 11.1 ml) and tetrakis(triphenylphosphine)palladium(0) (129 mg) in isopropanol (10 ml) was divided into three portions then stirred in sealed vials at 150° C. for 25 min in a microwave oven. The reaction mixtures were combined, the solvent was removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was separated using a hydrophobic filter tube, the solvent was evaporated and the residue was purified by chromatography on a silica column eluting with an ethyl acetate:cyclohexane gradient, to give the title compound as a yellow foam (1.76 g).

後処理

  1. customThe reaction mixtures
  2. customthe solvent was removed under vacuum
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. customthe solvent was evaporated
  6. customthe residue was purified by chromatography on a silica column
  7. washeluting with an ethyl acetate

出典と根拠

ORDレコード
ord-38c79a5b6eac44198382e48a4a5dfdf0
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07687532B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート