Benzyl Alcohol → 5-(Benzyloxy)-6-bromo-1H-indazole

HRID 1661995ノート

反応式

HRID 1661995 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[OH:11].[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[CH2:12]([O:11][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[Br:1])[NH:8][N:7]=[CH:6]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

8

反応物 5

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 5462977Diethyl azodicarboxylateHCID 591599466-Bromo-1H-indazol-5-ol

生成物 1

HCID 667670495-(Benzyloxy)-6-bromo-1H-indazole収率 70.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of 6-bromo-5-hydroxy-1H-indazole (5 g, 23.5 mmol) in THF (50 mL) is added benzyl alcohol (3.05 g, 28.2 mmol), PPh3 (7.39 g, 28.2 mmol) and diethylazodicarboxylate (4.46 mL, 28.2 mmol). After the reaction mixture is stirred at RT overnight, EtOAc (50 mL) and saturated aqueous NH4Cl (30 mL) are added. The organic phase is separated, dried over MgSO4, and concentrated. The residue is purified by silica gel column chromatography eluting with PE:EtOAc (4:1) to provide the product (5.0 g, 70.2% yield). MS (m/z): 303.0 (M+H).

後処理

  1. customThe organic phase is separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue is purified by silica gel column chromatography
  5. washeluting with PE

出典と根拠

ORDレコード
ord-808a9cc82f2145129a401af8e37a52d8
出典データセット
uspto-grants-2011_10
特許番号
US08030302B2

反応ノート

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