N,N,N',N'-Tetramethylethylenediamine → (2-[(tert-Butoxycarbonyl)amino]pyridin-3-yl)boronic acid

HRID 1930757노트

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HRID 1930757 반응식
[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].CN(C)CCN(C)C.C([Li])CCC.[B:28](OCC(C)C)([O:34]CC(C)C)[O:29]CC(C)C.[Cl-].[NH4+]>CCOCC.O1CCCC1>[C:1]([O:5][C:6]([NH:7][C:8]1[C:13]([B:28]([OH:34])[OH:29])=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:14])([CH3:4])([CH3:2])[CH3:3]

참가 물질

8

반응물 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 25517Ammonium ChlorideHCID 61587Triisobutyl borateHCID 112063492-(Boc-amino)pyridineHCID 178418339Butyllithium

생성물 1

HCID 22135186(2-[(tert-Butoxycarbonyl)amino]pyridin-3-yl)boronic acid수율 71.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

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온도
-70 °C

실험 절차

A solution of tetrahydrofuran (400 mL) of pyridin-2-yl-carbamic acid tert-butyl ester (16 g) described in Manufacturing Example 1-7-1 and N,N,N′,N′-tetramethylethylene diamine (25 g) was cooled to −70° C., n-butyl lithium (78 mL, 2.64 M heptane solution) was added dropwise for 1 hour, and the mixture was stirred for 10 minutes. This mixture was then warmed to between −10° C. and −6° C., and stirred at that temperature for 2 hours. The solution was then cooled again to −70° C., and triisobutyl borate (58 g) was added dropwise for 1 hour. The mixture was warmed to 0° C., and saturated aqueous ammonium chloride solution was added thereto. To the resulting yellow solids was added ether and then stirred, and the solids were filtered and washed with ether and water. The solids were dried under a reduced pressure to obtain the title compound (14 g).

후처리

  1. temperatureThis mixture was then warmed to between −10° C. and −6° C.
  2. stirringstirred at that temperature for 2 hours
  3. temperatureThe solution was then cooled again to −70° C.
  4. temperatureThe mixture was warmed to 0° C.
  5. stirringstirred
  6. filtrationthe solids were filtered
  7. washwashed with ether and water
  8. customThe solids were dried under a reduced pressure

출처 및 근거

ORD 기록
ord-0bdc8ad9c7b54110a1c9860c9ef7b31f
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188119B2

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