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

HRID 1038006노트

반응식

HRID 1038006 반응식
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

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 70394911HCID 70394911, 화합물용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3b030c67ac524dd68b2377a2e3658020
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546404B2

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