Potassium Acetate → (R)-1-Methyl-5-(5-(3-methylmorpholine-4-carbonyl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-ylboronic Acid

HRID 1185132노트

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HRID 1185132 반응식
Br[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][C@H:20]3[CH3:25])=[O:18])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[B:26]1(B2OC(C)(C)C(C)(C)O2)[O:30]C(C)(C)C(C)(C)[O:27]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])(=O)C.[K+]>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].O1CCOCC1>[CH3:8][N:6]1[C:5](=[O:9])[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][C@H:20]3[CH3:25])=[O:18])=[CH:13][N:12]=2)=[CH:3][C:2]([B:26]([OH:30])[OH:27])=[CH:7]1

참가 물질

7

반응물 4

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86683986(R)-5-Bromo-1-methyl-3-(5-(3-methylmorpholine-4-carbonyl)pyridin-2-ylamino)pyridin-2(1H)-one

생성물 1

HCID 86683988(R)-1-Methyl-5-(5-(3-methylmorpholine-4-carbonyl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-ylboronic Acid수율 94.6%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
70 °C

실험 절차

A 100-mL round-bottomed flask equipped with a reflux condenser was charged with 132b (580 mg. 1.42 mmol), bis(pinacolato)diboron (1.2 g, 4.5 mmol), Pd2(dba)3 (137 mg, 0.15 mmol), X-phos (71 mg, 0.15 mmol), potassium acetate (294 mg, 3.0 mmol), and 1,4-dioxane (20 mL). After three cycles of vacuum/argon flush, the mixture was heated at 70° C. for 2 h. Then it was filtered and the filtrate was evaporated under reduced pressure. The residue was washed with petroleum ether to afford 132c (500 mg, 94%) as a white solid, which was used in the next step without further purification. MS-ESI: [M+H]+ 373.1

후처리

  1. customA 100-mL round-bottomed flask equipped with a reflux condenser
  2. customAfter three cycles of vacuum/argon flush
  3. filtrationThen it was filtered
  4. customthe filtrate was evaporated under reduced pressure
  5. washThe residue was washed with petroleum ether

출처 및 근거

ORD 기록
ord-8fb0148c574c45e29efe8d14668813a9
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669251B2

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