Sodium Carbonate → N-tert-butyl-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

HRID 246664ノート

反応式

HRID 246664 の反応式
Br[C:2]1[N:7]=[C:6]2[C:8]([C:11]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:9][NH:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:26]2[CH:27]=[CH:28][CH:29]=[C:30]3[C:34]=2[N:33]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[N:32]=[CH:31]3)O1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:14]([NH:13][C:11]([C:8]1[C:6]2=[N:7][C:2]([C:26]3[CH:27]=[CH:28][CH:29]=[C:30]4[C:34]=3[N:33]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[N:32]=[CH:31]4)=[CH:3][N:4]=[C:5]2[NH:10][CH:9]=1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 712800667-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazoleHCID 866779952-bromo-N-tert-butyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

生成物 1

HCID 71280304N-tert-butyl-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide収率 76.6%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

A mixture of 2-bromo-N-tert-butyl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (0.1 g, 0.337 mmol), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (121 mg, 0.37 mmol), Pd2(dba)3 (39 mg, 0.067 mmol), X-Phos (64 mg, 0.135 mmol) and Na2CO3 (107 mg, 1.01 mmol) in dioxane (20 mL) and water (5 mL) was heated to 90° C. for 16 hours under N2 atmosphere. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate (20 mL) and water (10 mL), organic phase was washed with brine (10 mL) then dried over Na2SO4 and concentrated to afford N-tert-butyl-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (120 mg, crude) as yellow oil. LCMS: (M+H)+=465.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate (20 mL) and water (10 mL), organic phase
  3. washwas washed with brine (10 mL)
  4. dry with materialthen dried over Na2SO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-db63391edcff48818962a226d54c5f68
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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