Potassium Carbonate → 5-(3,5-Dimethyl-1H-pyrazol-4-yl)-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide

HRID 387351

反応式

Br[C:2]1[C:3]([CH3:8])=[N:4][NH:5][C:6]=1[CH3:7].[O:9]=[S:10]1(=[O:37])[CH2:15][CH2:14][CH:13]([C:16]2[C:24]3[C:19](=[C:20]([C:34]([NH2:36])=[O:35])[CH:21]=[C:22](B4OC(C)(C)C(C)(C)O4)[CH:23]=3)[NH:18][CH:17]=2)[CH2:12][CH2:11]1.C([O-])([O-])=O.[K+].[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.O>[CH3:8][C:3]1[C:2]([C:22]2[CH:23]=[C:24]3[C:19](=[C:20]([C:34]([NH2:36])=[O:35])[CH:21]=2)[NH:18][CH:17]=[C:16]3[CH:13]2[CH2:12][CH2:11][S:10](=[O:9])(=[O:37])[CH2:15][CH2:14]2)=[C:6]([CH3:7])[NH:5][N:4]=1

参加物

反応条件

温度: 120 °C

実験手順

4-Bromo-3,5-dimethyl-1H-pyrazole (35 mg, 0.2 mmol), 3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide (30 mg, 0.072 mmol) and K2CO3 (50 mg, 0.36 mmol) was taken up in a 3:1 mixture of 1,4-dioxane/water (2 mL) in a microwave vial. The mixture was degassed by bubbling argon through it for 5 min. PdCl2(dppf) (8 mg, 0.011 mmol) was added, and the reaction was heated in a microwave for 10 min at 120° C. The reaction mixture was concentrated, diluted in DMSO, and purified on a Gilson HPLC(NH4OH buffer), giving 3 mg (11%) of the title compound.

後処理

customThe mixture was degassed
customby bubbling argon through it for 5 min
concentrationThe reaction mixture was concentrated
additiondiluted in DMSO
custompurified on a Gilson HPLC(NH4OH buffer)

出典と根拠

ORDレコード: ord-2b5ab3d1e1174c0a85694469ecf2f654
出典データセット: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08372875B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 2

反応条件

実験手順

後処理

出典と根拠

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