Potassium Phosphate, Tribasic → Methyl 4-(6-bromoimidazo[1,2-a]pyridin-3-yl)benzoate

HRID 1792430노트

반응식

HRID 1792430 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)O1.[Br:20][C:21]1[CH:22]=[CH:23][C:24]2[N:25]([C:27](I)=[CH:28][N:29]=2)[CH:26]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O>[Br:20][C:21]1[CH:22]=[CH:23][C:24]2[N:25]([C:27]([C:9]3[CH:10]=[CH:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:17][CH:18]=3)=[CH:28][N:29]=2)[CH:26]=1

참가 물질

5

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 2773500Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 220316326-Bromo-3-iodoimidazo(1,2-a)pyridine

생성물 1

HCID 22031371Methyl 4-(6-bromoimidazo[1,2-a]pyridin-3-yl)benzoate수율 67.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2.3 g methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate prepared according to T. Ishiyama et al., J. Org. Chem., 60, 7508 (1995), 2.0 g 6-bromo-3-iodoimidazo[1,2-a]pyridine (compound in Production Example 49), 2.5 g potassium phosphate, 360 mg tetrakistriphenyl phosphine palladium and 30 mL N,N-dimethylformamide were heated at 100° C. under nitrogen atmosphere. Insolubles were filtered off, the solvent was removed, and the residue was purified by NH silica gel column chromatography (hexane/ethyl acetate) and recrystallized from ethyl acetate to give 1.39 g of the title compound (colorless crystals).

후처리

  1. filtrationInsolubles were filtered off
  2. customthe solvent was removed
  3. customthe residue was purified by NH silica gel column chromatography (hexane/ethyl acetate)
  4. customrecrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-87ea1ccdc5514c38a6a2a4a05e08cb86
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074801B1

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