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Triphenylphosphine → 2-(5-Amino-1-{3-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-1H-pyrazol-3-yl)-2-methyl-propionitrile

HRID 2200050
ノート
印刷プレビュー

反応式

HRID 2200050 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=2)[N:5]=[C:4]([C:14]([CH3:18])([CH3:17])[C:15]#[N:16])[CH:3]=1.[O:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[O:25][CH2:26][CH2:27]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:27][CH2:26][O:25][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][O:19]3)[CH:8]=2)[N:5]=[C:4]([C:14]([CH3:18])([CH3:17])[C:15]#[N:16])[CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylate2 回HCID 41668332-(Oxan-2-yloxy)ethan-1-olHCID 1177292592-[5-Amino-1-(3-hydroxy-phenyl)-1H-pyrazol-3-yl]-2-methyl-propionitrile

生成物 1

HCID 1177287572-(5-Amino-1-{3-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-1H-pyrazol-3-yl)-2-methyl-propionitrile収率 57%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To an ice cooled solution of Intermediate 20b (363 mg, 1.50 mmol), 2-(tetrahydro-2H-pyran-2-yloxy)ethanol (329 mg, 305 μL, 2.25 mmol) and triphenylphosphine (786 mg, 3.00 mmol) in anhydrous THF (10 mL) was added dropwise diisopropyl azodicarboxylate (606 mg, 590 μL), and the ice bath removed and stirring continued under an Ar atmosphere. After 3 h, a further 1.0 eq of diisopropyl azodicarboxylate was added and the reaction stirred overnight. The reaction mixture was then concentrated in vacuo and subjected to FCC, eluting with 5-50% EtOAc in cyclohexane. The isolated product was repurified using FCC, eluting with 2.5-7.5% Et2O in DCM, to afford the title compound as a yellow oil (317 mg, 57%). LCMS (Method 3): Rt 3.67 min, m/z 393.3 [M+Na].

後処理

  1. customthe ice bath removed
  2. stirringthe reaction stirred overnight
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. washeluting with 5-50% EtOAc in cyclohexane
  5. customThe isolated product was repurified
  6. washeluting with 2.5-7.5% Et2O in DCM

出典と根拠

ORDレコード
ord-31d7a239deb448f9aa8ef7bd59a146b6
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09359354B2

反応ノート

読み込み中…

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