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(R)-3-(4-Bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one → HCID 66668285、化合物

HRID 1617989
ノート
印刷プレビュー

反応式

HRID 1617989 の反応式
[I-].[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][CH:12]([Zn+])[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].Br[C:17]1[CH:22]=[CH:21][C:20]([C@H:23]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH3:40])[CH2:24][C:25]([C:27]2[CH:32]=[CH:31][N:30]=[C:29]([CH3:33])[CH:28]=2)=[O:26])=[CH:19][CH:18]=1>CN(C)C(=O)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[CH3:33][C:29]1[CH:28]=[C:27]([C:25](=[O:26])[CH2:24][C@H:23]([C:20]2[CH:21]=[CH:22][C:17]([CH:12]3[CH2:13][CH2:14][N:9]([C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:8])[CH2:10][CH2:11]3)=[CH:18][CH:19]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH3:40])[CH:32]=[CH:31][N:30]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 66666695(R)-3-(4-Bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-oneHCID 178452044HCID 178452044、化合物

生成物 1

HCID 66668285HCID 66668285、化合物収率 57%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418807
HCID 178418807、化合物
触媒
HCID 31374Dimethylacetamide溶媒

反応条件

温度
85 °C

実験手順

(1-(tert-Butoxycarbonyl)piperidin-4-yl) zinc(II) iodide solution (0.5 M in N,N-dimethylacetamide, 2.0 mL, 1.0 mmol; preparation according to J. Org. Chem. 2004, 69, 5120) was added at room temperature under argon to a mixture of (R)-3-(4-bromophenyl)-1-(2-methylpyridin-4-yl)-3-o-tolylpropan-1-one (example 142, step 2; 200 mg, 507 μmol), copper(I) iodide (9.7 mg, 51 μmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (18.6 mg, 25.4 μmol) in N,N-dimethylacetamide (3 mL). The reaction mixture was heated at 85° C., then after 4 h partitioned between sat. aq. ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) produced the title compound (144 mg, 57%). Off-white foam, MS (ESI+): m/z=499.3 ([M+H]+).

後処理

  1. customafter 4 h partitioned between sat. aq. ammonium chloride solution and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

出典と根拠

ORDレコード
ord-be294fec3cab40aea3896840fb1f625a
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08765730B2

反応ノート

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