2-Iodophenol → HCID 86668768, 화합물

HRID 533543노트

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HRID 533543 반응식
[CH3:1][C:2]([S:30]([CH3:33])(=[O:32])=[O:31])([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][CH:16]=1)[C:3]([NH:5][O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)=[O:4].Br[C:35]1[CH:36]=[CH:37][C:38](=[C:41]2[C:46](=[O:47])OC(C)(C)OC2=O)NC=1.IC1C=CC=CC=1O.[F-].[Cs+]>C(OCC)(=O)C.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.O1CCOCC1>[OH:47][C:46]1[CH:35]=[CH:36][CH:37]=[CH:38][C:41]=1[C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][C:2]([CH3:1])([S:30]([CH3:33])(=[O:32])=[O:31])[C:3]([NH:5][O:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)=[O:4])=[CH:20][CH:19]=1

참가 물질

9

반응물 4

HCID 107842-IodophenolHCID 25953Cesium fluorideHCID 574434985-(5-Bromopyridin-2(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 764453942-methanesulfonyl-2-methyl-N-(tetrahydro-pyran-2-yloxy)-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-butyramide

생성물 1

HCID 86668768HCID 86668768, 화합물

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
115 °C

실험 절차

To a flask containing 2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide prepared as in Preparation Number 3 (150 mg, 0.312 mmol) was added 2-iodophenol (89.3 mg, 0.406 mmol), cesium fluoride (190 mg, 1.25 mmol), water (500 uL) and 1,4-dioxane (3 mL). To this mixture was added Palladium tetrakis (54.3 mg, 0.047 mmol) and the mixture was heated to 115° C. with stirring overnight. The mixture was diluted with ethyl acetate and water. The phases were separated and the crude organic extract was concentrated in vacuo to dryness. The crude material was purified via silica gel chromatography eluting with ethyl acetate/heptanes to afford 4-(2′-hydroxybiphenyl-4-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide as solid. 19.6 mg LCMS: (M−1) 446.3.

후처리

  1. additionTo a flask containing
  2. customThe phases were separated
  3. extractionthe crude organic extract
  4. concentrationwas concentrated in vacuo to dryness
  5. customThe crude material was purified via silica gel chromatography
  6. washeluting with ethyl acetate/heptanes

출처 및 근거

ORD 기록
ord-0e2a7591f8aa451d900ec777da5c4044
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853258B2

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