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Ethyl Acetate → 5-(3-chlorophenyl)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine

HRID 715020
ノート
印刷プレビュー

反応式

HRID 715020 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[N:9][N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:5]2=[N:6][CH:7]=1.[Cl:21][C:22]1[CH:23]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:25]=[CH:26][CH:27]=1.C([O-])([O-])=O.[Cs+].[Cs+].C(OCC)(=O)C>COCCOC.CCCCCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:21][C:22]1[CH:27]=[C:26]([C:2]2[CH:3]=[C:4]3[C:10]([CH3:11])=[N:9][N:8]([CH2:12][C:13]4[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=4)[C:5]3=[N:6][CH:7]=2)[CH:25]=[CH:24][CH:23]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 100372252-(3-Chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 578563335-bromo-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine

生成物 1

HCID 683885505-(3-chlorophenyl)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 8058Hexane溶媒
HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of 5-bromo-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine (7) (100 mg, 0.301 mmol, 1 eq) and 2-(3-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (95) (71 mg, 0.301 mmol, 1 eq) in 1,2-dimethoxyethane (10 mL) was added Cs2CO3 (244 mg, 0.752 mmol, 25 eq) 2M aqueous solution followed by degassing, purging with N2 for 15 min and addition of Pd(PPh3)4 (13 mg, 0.012 mmol, 0.04 eq). The reaction mixture was heated at 100° C. in a sealed tube overnight. After completion of the reaction the mixture was partitioned between ethyl acetate and water and the organic layer was separated and again extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate and the solvent completely distilled off to get the crude. The crude was passed through 100-200 mesh silica gel eluting the pure compound at 50% ethyl acetate in hexane as off-white coloured solid compound 96 (60 mg).

後処理

  1. customby degassing
  2. custompurging with N2 for 15 min
  3. customAfter completion of the reaction the mixture
  4. customwas partitioned between ethyl acetate and water
  5. customthe organic layer was separated
  6. extractionagain extracted with ethyl acetate
  7. dry with materialThe combined organic layers were dried over sodium sulphate
  8. distillationthe solvent completely distilled off
  9. customto get the crude

出典と根拠

ORDレコード
ord-95db4a312f764c3893fa4db7ee1101c0
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09187473B2

反応ノート

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