Nitrogen → HCID 86700717、化合物

HRID 572480ノート

反応式

HRID 572480 の反応式
Br[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[O:12])[O:4][C:3]=1[C@H:13]([OH:33])[CH2:14][O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][C:40]=1[CH3:41].N#N.C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O.CCOC(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>[Si:16]([O:15][CH2:14][C@H:13]([C:3]1[O:4][C:5](=[O:12])[C:6]2[C:7]([C:2]=1[C:37]1[CH:38]=[CH:39][C:40]([CH3:41])=[C:35]([CH3:34])[CH:36]=1)=[CH:8][CH:9]=[CH:10][CH:11]=2)[OH:33])([C:29]([CH3:30])([CH3:31])[CH3:32])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

8

反応物 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 27343483,4-Dimethylphenylboronic acidHCID 68294919HCID 68294919、化合物

生成物 1

HCID 86700717HCID 86700717、化合物収率 62%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 4-bromo-3-((1R)-2-{[(1,1-dimethylethyl)(diphenyl)silyl]oxy}-1-hydroxyethyl)-1H-2-benzopyran-1-one (142 mg, 0.271 mmol) and 3,4-dimethylphenylboronic acid (61.0 mg, 0.407 mmol) in N,N-Dimethylformamide (DMF) (2.5 mL) was degassed with N2 for 10 min. The reaction mixture was treated with 2M Na2CO3 (149 μl, 0.298 mmol) and Pd(PPh3)4 (16 mg, 0.014 mmol) and irradiated in the microwave for 20 min at 120° C. The reaction mixture was diluted with EtOAc, and washed with saturated aqueous NH4Cl, brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel chromatography (ethyl acetate-hexanes 0-30%) to afford the title compound (92 mg, 0.168 mmol, 62% yield) as a white solid: Rt=1.31, 1.33 (atropisomers), ES+ MS: 571 (M+23).

後処理

  1. customirradiated in the microwave for 20 min at 120° C
  2. washwashed with saturated aqueous NH4Cl, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (ethyl acetate-hexanes 0-30%)

出典と根拠

ORDレコード
ord-73385b61a6f841aebf7c2ec077c97425
出典データセット
uspto-grants-2015_05
特許番号
US09029391B2

反応ノート

読み込み中…