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Cesium carbonate → {4-[4-bromo-1-(2-methylpropyl)-1H-benzotriazol-5-yl]phenyl}methanol

HRID 2281057
ノート
印刷プレビュー

反応式

HRID 2281057 の反応式
[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1I.[OH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21](B2OC(C)(C)C(C)(C)O2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.O.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:21]1[CH:22]=[CH:23][C:18]([CH2:17][OH:16])=[CH:19][CH:20]=1
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

8

反応物 3

HCID 10796Cesium carbonateHCID 114020504-(Hydroxymethyl)benzeneboronic acid pinacol esterHCID 709780934-Bromo-5-iodo-1-(2-methylpropyl)-1H-benzotriazole

生成物 1

HCID 68657365{4-[4-bromo-1-(2-methylpropyl)-1H-benzotriazol-5-yl]phenyl}methanol

試薬・触媒・溶媒 4

HCID 178418807HCID 178418807、化合物触媒
HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

4-Bromo-5-iodo-1-(2-methylpropyl)-1H-benzotriazole (554 mg, 1.458 mmol), 4-(hydroxymethyl)benzeneboronic acid pinacol ester (325 mg, 1.388 mmol), PdCl2(dppf)-dichloromethane adduct (56.7 mg, 0.069 mmol) and cesium carbonate (1357 mg, 4.16 mmol) were combined in tetrahydrofuran (7 ml) and water (0.700 ml). The vessel was sealed and heated at 40° C. for 48 hours. The mixture was cooled to ambient temperature, diluted with ethyl acetate, filtered through Celite and concentrated in vacuo. The residue was purified via silica gel chromatography (ethyl acetate/hexane gradient), providing the titled compound as white foam. LRMS m/z (M+H) 359.9 and 361.9 found, 360.06 and 362.06 required.

後処理

  1. customThe vessel was sealed
  2. temperatureThe mixture was cooled to ambient temperature
  3. filtrationfiltered through Celite
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via silica gel chromatography (ethyl acetate/hexane gradient)

出典と根拠

ORDレコード
ord-d562e9bea4b4490e9317de3b39706036
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09139576B2

反応ノート

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