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1-Cyclohexenylboronic acid → 4-[5-Amino-6-(1-cyclohexen-1-yl)-2-pyridinyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester

HRID 1445262
ノート
印刷プレビュー

反応式

HRID 1445262 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16](Br)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]1(B(O)O)[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]=1>CCO.C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+].CCOCC.[Cl-].[Na+].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>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([C:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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

9

反応物 2

HCID 38629021-Cyclohexenylboronic acidHCID 591286051,1-Dimethylethyl 4-(5-amino-6-bromo-2-pyridinyl)-1-piperidinecarboxylate

生成物 1

HCID 591285794-[5-Amino-6-(1-cyclohexen-1-yl)-2-pyridinyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester収率 74.6%

試薬・触媒・溶媒 6

HCID 178418397HCID 178418397、化合物触媒
HCID 702
Ethanol
溶媒
HCID 1140Toluene溶媒
HCID 3283Diethyl Ether溶媒
HCID 10340Sodium Carbonate溶媒
HCID 57417360Sodium chloride; water溶媒

反応条件

温度
80 °C

実験手順

To a mixture of 5-amino-6-bromo-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (331 mg, 0.93 mmol) (as prepared in Example 54, step (c)) and cyclohexen-1-yl boronic acid (141 mg, 1.11 mmol) in 5 mL of EtOH, 10 mL of toluene and 5 mL of 2 M Na2CO3, was added Pd(PPh3)4 (107 mg, 0.0930 mmol) and the result was heated at 80° C. for 16 h. The reaction was diluted with 100 mL of ether and 100 mL of brine and the layers were separated. The organic layer was dried (Na2SO4) and concentrated in vacuo. Purification of the residue by column chromatography (silica gel, 30-60% ether-hexanes) afforded 248 mg (74%) the title compound as an light brown oil LC-MS (ESI, m/z): Calcd. for C21H32N3O2(M+H), 358.2, found 358.1.

後処理

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by column chromatography (silica gel, 30-60% ether-hexanes)

出典と根拠

ORDレコード
ord-c83ef30488f24cbfaad110dee8336754
出典データセット
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07662837B2

反応ノート

読み込み中…

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