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Cesium carbonate → Methyl 3-[[3-[4-[tert-butyl(dimethyl)silyl]oxy-1-piperidyl]naphthalene-1-carbonyl]amino]-2,4-dimethyl-benzoate

HRID 1427138
ノート
印刷プレビュー

反応式

HRID 1427138 の反応式
Br[C:2]1[CH:3]=[C:4]([C:12]([NH:14][C:15]2[C:16]([CH3:26])=[C:17]([CH:22]=[CH:23][C:24]=2[CH3:25])[C:18]([O:20][CH3:21])=[O:19])=[O:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:27]([Si:31]([CH3:40])([CH3:39])[O:32][CH:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)([CH3:30])([CH3:29])[CH3:28].C([O-])([O-])=O.[Cs+].[Cs+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>O1CCOCC1.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]>[Si:31]([O:32][CH:33]1[CH2:34][CH2:35][N:36]([C:2]2[CH:3]=[C:4]([C:12]([NH:14][C:15]3[C:16]([CH3:26])=[C:17]([CH:22]=[CH:23][C:24]=3[CH3:25])[C:18]([O:20][CH3:21])=[O:19])=[O:13])[C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:37][CH2:38]1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:40])[CH3:39]
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

7

反応物 4

HCID 10796Cesium carbonateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 114813284-((Tert-butyldimethylsilyl)oxy)piperidineHCID 86707371Methyl 3-[(3-bromonaphthalene-1-carbonyl)amino]-2,4-dimethyl-benzoate

生成物 1

HCID 86707372Methyl 3-[[3-[4-[tert-butyl(dimethyl)silyl]oxy-1-piperidyl]naphthalene-1-carbonyl]amino]-2,4-dimethyl-benzoate
収率 86.5%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

To a solution of methyl 3-(3-bromo-1-naphthamido)-2,4-dimethylbenzoate (0.48 g, 0.0011 mol), tert-butyl-dimethyl-(4-piperidyloxy)silane (0.75 g, 0.0034 mol, see preparation 3) and Cs2CO3 (1.00 g, 0.0033 mol) in 1,4-dioxane (8 ml) is added Pd2(dba)3 (0.10 g, 0.00011 mol) followed by S-Phos (0.045 g, 0.00011 mol). The reaction mixture is purged with nitrogen for 5 minutes and then stirred at 80° C. After 16 hours, the reaction is cooled to ambient temperature, filtered through Celite™ and washed with EtOAc. The organic layers are combined and dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound as a black semi-solid (0.52 g, crude). Mass spectrum (m/z): 547.5 (M+1).

後処理

  1. customThe reaction mixture is purged with nitrogen for 5 minutes
  2. temperaturethe reaction is cooled to ambient temperature
  3. filtrationfiltered through Celite™
  4. washwashed with EtOAc
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-55aec51dd2ed4b41be885a89a8595080
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08933098B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート