Sodium Carbonate → tert-butyl 4-(5-cyclopropyl-3-ethynyl-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 387534ノート

反応式

HRID 387534 の反応式
[CH:1]1([C:4]2[C:5]([N:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]3)=[C:6]3[C:12]([C:13]#[C:14][Si](C)(C)C)=[N:11][N:10]([CH2:19][C:20]4[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=4)[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH:1]1([C:4]2[C:5]([N:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]3)=[C:6]3[C:12]([C:13]#[CH:14])=[N:11][N:10]([CH2:19][C:20]4[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=4)[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 68769357tert-butyl 4-(5-cyclopropyl-1-(4-methoxybenzyl)-3-((trimethylsilyl)ethynyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

生成物 1

HCID 86647261tert-butyl 4-(5-cyclopropyl-3-ethynyl-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate収率 102.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

tert-Butyl 4-(5-cyclopropyl-1-(4-methoxybenzyl)-3-((trimethylsilyl)ethynyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (280 mg, 0.50 mmol) was placed in THF (8 mL) at 0° C. TBAF (0.54 mL, 0.54 mmol) was then added, and the reaction stirred for 30 minutes at room temperature. The reaction was then poured into saturated Na2CO3, and extracted with DCM. The combined organic fractions were dried, filtered, and concentrated to give the crude product, which was purified by column chromatography to give tert-butyl 4-(5-cyclopropyl-3-ethynyl-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (250 mg, 96% yield).

後処理

  1. extractionextracted with DCM
  2. customThe combined organic fractions were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-53bf62f3cdec41a9b025a5d8ace2297f
出典データセット
uspto-grants-2013_02
特許番号
US08372842B2

反応ノート

読み込み中…