Potassium Phosphate, Tribasic → HCID 59565188, 화합물

HRID 2067017노트

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HRID 2067017 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[N:12][CH:13]=[C:7]2[C:6]=1Cl)=[O:4].[Br:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([F:23])[CH:17]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[N:12][CH:13]=[C:7]2[C:6]=1[NH:20][C:19]1[CH:21]=[CH:22][C:16]([Br:15])=[CH:17][C:18]=1[F:23])=[O:4]

참가 물질

6

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 1230504-Bromo-2-fluoroanilineHCID 59565199Methyl 8-chloroimidazo[1,5-a]pyridine-7-carboxylate

생성물 1

HCID 59565188HCID 59565188, 화합물수율 28%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

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온도
100 °C

실험 절차

A suspension of 8-chloro-imidazo[1,5-a]pyridine-7-carboxylic acid methyl ester (500 mg, 2.38 mmol), 4-bromo-2-fluoroaniline (543 mg, 2.86 mmol), Pd2dba3 (110 mg, 0.12 mmol), 2-dicyclohexylFphosphino-2′,6′-diisopropoxybiphenyl (224 mg, 0.48 mmol) and K3PO4 (710 mg, 3.33 mmol) in toluene (10 mL) was degassed and then heated at 100° C. for 18 hours. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate and filtered. The filtrate was washed with water and brine, then loaded onto a 10 g Isolute® SCX-2 cartridge which was eluted with methanol and then a 2M solution of ammonia in methanol. The appropriate fractions were combined and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si-PPC, gradient 0% to 20%, ethyl actetate in DCM) to afford the title compound as a yellow oil (240 mg, 28%). LCMS (method B): RT=3.40 min, [M+H]+=364/366.

후처리

  1. customwas degassed
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. additiondiluted with ethyl acetate
  4. filtrationfiltered
  5. washThe filtrate was washed with water and brine
  6. washwas eluted with methanol
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8c602adfe6984ea9ae09f7c8341e3268
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293763B2

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