Ethyl Acetate → HCID 57906615, 화합물

HRID 420521노트

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HRID 420521 반응식
[CH3:1][O:2][C:3]([C:5]1[C:10](Br)=[CH:9][N:8]2[CH:12]=[CH:13][N:14]=[C:7]2[CH:6]=1)=[O:4].[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>COCCOC.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>[CH3:1][O:2][C:3]([C:5]1[C:10]([C:19]2[CH:18]=[CH:17][C:16]([Cl:15])=[CH:21][C:20]=2[Cl:22])=[CH:9][N:8]2[CH:12]=[CH:13][N:14]=[C:7]2[CH:6]=1)=[O:4]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 57906576Methyl 6-bromoimidazo[1,2-a]pyridine-7-carboxylate

생성물 1

HCID 57906615HCID 57906615, 화합물수율 77%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

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온도
150 °C

실험 절차

In a sealed tube, a mixture of 6-bromo-imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (505 mg, 1.98 mmol), 2,4-dichlorobenzeneboronic acid (416 mg, 2.18 mmol), Pd(PPh3)4 (114 mg, 0.10 mmol) and Na2CO3 (2.0 M solution in water, 3.5 mL) in DME (5 mL) was heated at 150° C. for 17 min in a microwave oven. The reaction mixture was cooled to RT, poured into AcOEt and washed with water. The organic layer was dried over Na2SO4, filtered, and evaporated. The remaining residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→100% TBME) to yield the title compound (488 mg, 1.52 mmol, 77%). MS: 321 [M+1]+; HPLC: AtRet=1.43; TLC: RF 0.16 (hexane/DCM/TBME 1:1:2).

후처리

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe remaining residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→100% TBME)

출처 및 근거

ORD 기록
ord-612b32a7c1c14abd934371b93b901d6e
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097617B2

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