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Lithium Hydroxide → HCID 67361802, 화합물

HRID 1183175
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HRID 1183175 반응식
COC(C1C=C(O)N(C2C=CC=CC=2F)N=1)=O.C(=O)([O-])[O-].[Cs+].[Cs+].BrCC1C=CC=CC=1C#N.C[O:35][C:36]([C:38]1[CH:42]=[C:41]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[C:51]#[N:52])[N:40]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[F:59])[N:39]=1)=[O:37].[OH-].[Li+]>CN(C=O)C.C1COCC1.O>[C:51]([C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=1[CH2:44][O:43][C:41]1[N:40]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[F:59])[N:39]=[C:38]([C:36]([OH:37])=[O:35])[CH:42]=1)#[N:52]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 3939Lithium HydroxideHCID 10796Cesium carbonateHCID 895992-(Bromomethyl)benzonitrileHCID 71257690HCID 71257690, 화합물HCID 178498589HCID 178498589, 화합물

생성물 1

HCID 67361802HCID 67361802, 화합물수율 86.4%

시약·촉매·용매 3

HCID 962Water용매
HCID 6228Dimethylformamide용매
HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

1-(2-Fluoro-phenyl)-5-hydroxy-1H-pyrazole-3-carboxylic acid methyl ester (200 mg, 0.847 mmol) were dissolved in 5 ml of DMF and cesium carbonate (552 mg, 1.7 mmol) and 2-bromomethyl-benzonitrile (166 mg, 0.85 mmol) were added. The mixture was stirred for 5 h at 60° C., filtrated and the solvent was removed in vacuo. The obtained residue of crude 5-(2-cyano-benzyloxy)-1-(2-fluoro-phenyl)-1H-pyrazole-3-carboxylic acid methyl ester (235 mg, 79%) was dissolved in a mixture of THF, MOH and water (3 ml each), lithium hydroxide (64.1 mg, 2.7 mmol) was added, and the mixture was stirred overnight at room temperature. After evaporation of the solvent the residue was subjected to column chromatography (silica gel, DCM/MOH 9:1) to give 195 mg (86%) of the title compound.

후처리

  1. filtrationfiltrated
  2. customthe solvent was removed in vacuo
  3. additionwas added
  4. stirringthe mixture was stirred overnight at room temperature
  5. customAfter evaporation of the solvent the residue

출처 및 근거

ORD 기록
ord-0cd5b384b5864f668dd840a368fa0883
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08664257B2

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