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

HRID 2281057
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인쇄 미리보기

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HRID 2281057 반응식
[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
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참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 178418807HCID 178418807, 화합물촉매
HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

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온도
40 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d562e9bea4b4490e9317de3b39706036
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09139576B2

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