Sodium Carbonate → 3-(1H-imidazo[4,5-b]pyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamine

HRID 241413

反応式

HRID 241413 の反応式
Br[C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:12]([N:17]=2)=[N:13][CH:14]=[CH:15][CH:16]=3)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:18][N:19]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:21]=[N:20]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.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>[NH:10]1[C:11]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[N:17]=[C:9]1[C:4]1[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([C:22]2[CH:21]=[N:20][N:19]([CH3:18])[CH:23]=2)[CH:3]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 668698105-bromo-3-(1H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-ylamine

生成物 1

HCID 668985513-(1H-imidazo[4,5-b]pyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamine

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

58 mg (0.200 mmol) of 5-bromo-3-(1H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-ylamine and 45.8 mg (0.220 mmol) of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole are suspended in 2 ml of N,N-dimethylformamide in a nitrogen-filled microwave vessel, and 0.57 ml (1.142 mmol) of 2M sodium carbonate solution and 23.1 mg (0.020 mmol) of tetrakis(triphenylphosphine)palladium(0) are added. The reaction solution is irradiated with microwaves for 30 min at 120° C. in the Biotage SmithSynthesizer. The reaction mixture is evaporated to dryness, and the residue is purified by means of RP-HPLC, giving 3-(1H-imidazo[4,5-b]pyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamine; HPLC-MS [M+H]+ 292.2;

後処理

  1. additionfilled microwave vessel
  2. customThe reaction solution is irradiated with microwaves for 30 min at 120° C. in the Biotage SmithSynthesizer
  3. customThe reaction mixture is evaporated to dryness
  4. customthe residue is purified by means of RP-HPLC

出典と根拠

ORDレコード
ord-a1ef29d4a7fb4ec281e9f0fd034bb37c
出典データセット
uspto-grants-2014_02
特許番号
US08648201B2

関連ノート

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