Ethyl Acetate → 6'-(Cyclohexyloxy)-5-fluoro-3,3'-bipyridin-2-amine

HRID 1405754

反応式

HRID 1405754 の反応式
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.[CH:10]1([O:16][C:17]2[N:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[Na+].[Na+].CCOC(C)=O>COCCOC.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>[CH:10]1([O:16][C:17]2[N:22]=[CH:21][C:20]([C:2]3[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=3)=[CH:19][CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 161264343-Bromo-5-fluoropyridin-2-amineHCID 66747855B-[6-(cyclohexyloxy)-3-pyridinyl]Boronic acid

生成物 1

HCID 667488416'-(Cyclohexyloxy)-5-fluoro-3,3'-bipyridin-2-amine収率 93.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

Tetrakis(triphenylphosphine)palladium(0) (36.3 mg) was added to a suspension of 3-bromo-5-fluoropyridin-2-amine (200 mg), 6-(cyclohexyloxy)pyridin-3-ylboronic acid (255 mg) and sodium carbonate (222 mg) in DME (5 mL) and water (1 mL) and the mixture was stirred at 90° C. under nitrogen for 3 hr. Water and EtOAc were added and the organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) and washed with IPE to give the title compound (280 mg) as a yellow solid.

後処理

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)
  6. washwashed with IPE

出典と根拠

ORDレコード
ord-e3fc5272606a4ade93e7d1678a58fd9f
出典データセット
uspto-grants-2014_12
特許番号
US08916551B2

関連ノート

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