9-Methoxy-9-borabicyclo(3.3.1)nonane → HCID 178498804、化合物

HRID 245637

反応式

HRID 245637 の反応式
[CH3:1]OB1C2CCCC1CCC2.C[Li].[CH3:14][O:15][C:16]([C:18]1[C:19]([NH2:29])=[C:20]([Cl:28])[CH:21]=[C:22]2[C:26]=1[NH:25][N:24]=[C:23]2Br)=[O:17]>O1CCCC1.C(OCC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Cl-].[Pd+2]>[CH3:14][O:15][C:16]([C:18]1[C:19]([NH2:29])=[C:20]([Cl:28])[CH:21]=[C:22]2[C:26]=1[NH:25][N:24]=[C:23]2[CH3:1])=[O:17]

参加物

7

反応物 3

HCID 5449649-Methoxy-9-borabicyclo(3.3.1)nonaneHCID 178418348HCID 178418348、化合物HCID 178498803HCID 178498803、化合物

生成物 1

HCID 178498804HCID 178498804、化合物収率 66%

試薬・触媒・溶媒 3

HCID 84124Bis(triphenylphosphine)palladium chloride触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 899 mg (5.91 mmol) of 9-methoxy-9-bora-bicyclo[3.3.1]nonane in 5 mL of anhydrous tetrahydrofuran is added dropwise 3.71 mL (5.91 mmol) of a solution 1N of methyl lithium in diethylether. After few minutes of stirring, a mixture of 6-amino-3-bromo-5-chloro-1H-indazole-7-carboxylic acid methyl ester, prepared as in step a in example 39, and 104 mg (0.15 mmol) of bis(triphenylphosphine) palladiumI(II) dichloride in 10 mL of anhydrous tetrahydrofuran is added. The reaction mixture is stirred in a microwave oven at 150° C. for 15 minutes. After filtration over Celite and concentration in vacuo, the residue is purified by flash chromatography (SiO2, hexanes/ethyl acetate 1:1) to afford 470 mg of product (66%) as a pale yellowish solid; LC/MS:240/242 (M+H)+.

後処理

  1. additionis added
  2. stirringThe reaction mixture is stirred in a microwave oven at 150° C. for 15 minutes
  3. filtrationAfter filtration
  4. concentrationover Celite and concentration in vacuo
  5. customthe residue is purified by flash chromatography (SiO2, hexanes/ethyl acetate 1:1)

出典と根拠

ORDレコード
ord-08bef5de52894447a2b63c14211b6865
出典データセット
uspto-grants-2014_02
特許番号
US08658801B2

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