Water → 2-Cyano-2''-hydroxymethyl-4-methyl-[1,1';3',1'']terphenyl-5'-carboxylic acid ethyl ester

HRID 2278726노트

반응식

HRID 2278726 반응식
Br[C:2]1[CH:3]=[C:4]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=2[C:15]#[N:16])[CH:7]=1.[OH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O.[C:32](=O)([O-])[O-].[Cs+].[Cs+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH2:20]([O:19][C:17]([C:4]1[CH:3]=[C:2]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH2:22][OH:21])[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=2[C:15]#[N:16])[CH:5]=1)=[O:18])[CH3:32]

참가 물질

7

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 43742622-(Hydroxymethyl)phenylboronic AcidHCID 58449349Methyl 5-bromo-2'-cyano-4'-methylbiphenyl-3-carboxylate

생성물 1

HCID 1176665832-Cyano-2''-hydroxymethyl-4-methyl-[1,1';3',1'']terphenyl-5'-carboxylic acid ethyl ester

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

실험 절차

Into a 5 mL microwave vial were charged methyl 5-bromo-2′-cyano-4′-methylbiphenyl-3-carboxylate (95 mg, 0.29 mmol), 2-(hydroxymethyl)phenylboronic acid (87 mg, 0.57 mmol), cesium carbonate (466 mg, 1.43 mmol), tetra-n-butylammonium iodide (106 mg, 0.29 mmol), POPd (14 mg, 0.029 mmol), water (0.2 mL) and N,N-dimethylformamide (1 mL). The reaction mixture was subjected to microwave irradiation for 10 mins at 150° C. After cooling, the reaction mixture was extracted with ethylacetate. The organic layer was washed with brine, dried, and concentrated under reduced pressure to give the residue which was purified by HPLC to yield the title compound.

후처리

  1. customirradiation for 10 mins at 150° C
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with ethylacetate
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto give the residue which
  8. customwas purified by HPLC

출처 및 근거

ORD 기록
ord-bd2fb6ee09e64b0cb4204b7179b23921
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133122B2

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