Potassium Acetate → 3-(Acetoxymethyl)-2-(10-fluoro-1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)pyridin-4-ylboronic Acid

HRID 592939ノート

反応式

HRID 592939 の反応式
[C:1]([O:4][CH2:5][C:6]1[C:7]([N:13]2[CH2:26][CH2:25][N:16]3[C:17]4[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=4[C:23]([F:24])=[C:15]3[C:14]2=[O:27])=[N:8][CH:9]=[CH:10][C:11]=1Cl)(=[O:3])[CH3:2].[B:28]1(B2OC(C)(C)C(C)(C)O2)[O:32]C(C)(C)C(C)(C)[O:29]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])(=O)C.[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[C:1]([O:4][CH2:5][C:6]1[C:7]([N:13]2[CH2:26][CH2:25][N:16]3[C:17]4[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=4[C:23]([F:24])=[C:15]3[C:14]2=[O:27])=[N:8][CH:9]=[CH:10][C:11]=1[B:28]([OH:32])[OH:29])(=[O:3])[CH3:2]

参加物

7

反応物 4

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86684433(4-Chloro-2-(10-fluoro-1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)pyridin-3-yl)methyl Acetate

生成物 1

HCID 866844343-(Acetoxymethyl)-2-(10-fluoro-1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)pyridin-4-ylboronic Acid収率 67.1%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
65 °C

実験手順

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 231b (600 mg, 1.53 mmol), Pin2B2 (1.94 g, 7.65 mmol), PdCl2(dppf) (65 mg, 0.080 mmol), X-Phos (73 mg, 0.15 mmol), potassium acetate (304 mg, 3.1 mmol), and dioxane (30 mL). After three cycles of vacuum/argon flush, the mixture was heated at 65° C. for 5 h. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was washed with petroleum ether to afford 231c (412 mg, 67%) as yellow solid. MS-ESI: [M+H]+ 402.1

後処理

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. customAfter three cycles of vacuum/argon flush
  3. temperatureIt was then cooled to room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washthe resulting residue was washed with petroleum ether

出典と根拠

ORDレコード
ord-943d2aec05534a8b9b98b083a8b3d028
出典データセット
uspto-grants-2016_01
特許番号
US09238655B2

反応ノート

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