Sodium Carbonate → (1R,3S)-methyl 3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-1-methylcyclohexanecarboxylate

HRID 527028ノート

反応式

HRID 527028 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][CH2:12][C@@:11]([CH3:19])([C:15]([O:17][CH3:18])=[O:16])[CH2:10]2)[C:5]([F:20])=[CH:4][N:3]=1.[Cl:21][C:22]1[CH:23]=[C:24]2[C:30](B3OC(C)(C)C(C)(C)O3)=[CH:29][N:28]([S:40]([C:43]3[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=3)(=[O:42])=[O:41])[C:25]2=[N:26][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O>[Cl:21][C:22]1[CH:23]=[C:24]2[C:30]([C:2]3[N:7]=[C:6]([NH:8][C@H:9]4[CH2:14][CH2:13][CH2:12][C@@:11]([CH3:19])([C:15]([O:17][CH3:18])=[O:16])[CH2:10]4)[C:5]([F:20])=[CH:4][N:3]=3)=[CH:29][N:28]([S:40]([C:43]3[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=3)(=[O:41])=[O:42])[C:25]2=[N:26][CH:27]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 575977475-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 86667436(1R,3S)-methyl 3-(2-chloro-5-fluoropyrimidin-4-ylamino)-1-methylcyclohexanecarboxylate2 回

生成物 1

HCID 68008233(1R,3S)-methyl 3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-1-methylcyclohexanecarboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

In a 25 mL round-bottomed flask were combined (1R,3S)-methyl 3-(2-chloro-5-fluoropyrimidin-4-ylamino)-1-methylcyclohexanecarboxylate, 52h, (0.061 g, 0.202 mmol), 5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine (0.096 g, 0.222 mmol), disodium carbonate (0.064 g, 0.607 mmol) in 5 mL of THF and 1 ml of water. The reaction mixture was degassed via a stream of nitrogen. To the reaction was added tetrakis triphenyl phosphine palladium (0) (0.021 g, 0.202 mmol) and the reaction was stirred at reflux overnight. The reaction was concentrated in vacuo and purified by silica gel chromatography (4:1 Hexanes:EtOAc), yielding 85 mg of desired product, 52i.

後処理

  1. customIn a 25 mL round-bottomed flask were combined
  2. customThe reaction mixture was degassed via a stream of nitrogen
  3. temperatureat reflux overnight
  4. concentrationThe reaction was concentrated in vacuo
  5. custompurified by silica gel chromatography (4:1 Hexanes:EtOAc)

出典と根拠

ORDレコード
ord-81a6949858644d25809cb65f09a601fa
出典データセット
uspto-grants-2016_05
特許番号
US09345708B2

反応ノート

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