2-Iodophenol → HCID 86668768、化合物

HRID 533543ノート

反応式

HRID 533543 の反応式
[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

参加物

9

反応物 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

生成物 1

HCID 86668768HCID 86668768、化合物

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
115 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0e2a7591f8aa451d900ec777da5c4044
出典データセット
uspto-grants-2014_10
特許番号
US08853258B2

反応ノート

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