Cesium carbonate → 2-(6-Bromopyridin-3-yl)pyrimidine

HRID 1038006

反応式

HRID 1038006 の反応式
Br[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][N:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CO.C1(C)C=CC=CC=1.O.CCOC(C)=O.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>[Br:8][C:9]1[N:10]=[CH:11][C:12]([C:2]2[N:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:13][CH:14]=1

参加物

8

反応物 3

HCID 10796Cesium carbonateHCID 783452-BromopyrimidineHCID 27627062-Bromopyridine-5-boronic acid

生成物 1

HCID 534869812-(6-Bromopyridin-3-yl)pyrimidine

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 70394911HCID 70394911、化合物溶媒

実験手順

A mixture of 2-bromopyrimidine (0.43 g, 2.70 mmol), 2-bromopyridine-5-boronic acid (0.55 g, 2.72 mmol), tetrakis(triphenylphosphine)palladium(0) (300 mg, 0.259 mmol), cesium carbonate (1.15 g, 3.03 mmol) was stirred in MeOH/toluene/water (15 ml, 1/1/1) at reflux temperature overnight. The reaction was cooled to room temperature and diluted with EtOAc (200 ml) and water (50 ml). The organic layer was separated, dried over MgSO4, filtered and solvent evaporated yielding a residue which was purified on silica gel eluting with 25% v/v EtOAc/hexanes yielding product 76 as white solid. (0.55 g, 85%) ESMS (MH, 236).

後処理

  1. temperatureat reflux temperature overnight
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customsolvent evaporated
  6. customyielding a residue which
  7. customwas purified on silica gel eluting with 25% v/v EtOAc/hexanes yielding product 76 as white solid

出典と根拠

ORDレコード
ord-3b030c67ac524dd68b2377a2e3658020
出典データセット
uspto-grants-2013_10
特許番号
US08546404B2

関連ノート

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