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

HRID 2278726ノート

反応式

HRID 2278726 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bd2fb6ee09e64b0cb4204b7179b23921
出典データセット
uspto-grants-2015_09
特許番号
US09133122B2

反応ノート

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