Hydrochloric Acid → HCID 136352222、化合物

HRID 1853263ノート

反応式

HRID 1853263 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[N:22][OH:23])[CH:7]=[C:8]([C:12]3[N:13]=[CH:14][C:15]4[C:20]([CH:21]=3)=[CH:19][CH:18]=[CH:17][CH:16]=4)[O:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:31]1([C:37]#[CH:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.Cl>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[CH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[C:12]([C:8]2[O:9][C:10]3[C:5]([C:6](=[N:22][OH:23])[CH:7]=2)=[CH:4][CH:3]=[C:2]([C:38]#[C:37][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:11]=3)[N:13]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 136352218HCID 136352218、化合物

生成物 1

HCID 136352222HCID 136352222、化合物収率 13.2%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A solution of 7-bromo-2-isoquinolin-3-yl-chromen-4-one oxime (52 mg, 0.142 mmol), trans-dichlorobis(triphenylphosphine)palladium (10 mg, 0.014 mmol), copper iodide (5.3 mg, 0.028 mmol) in dimethylformamide (3 ml) was degassed with argon for 10 min and then treated with triethylamine (30 μl, 0.213 mmol) and phenyl acetylene (19 μl, 0.170 mmol). The solution was warmed to 90° C. for 18 hours and then poured onto a 0.5N aqueous solution of hydrogen chloride, extracted with ethyl acetate and purified by preparative HPLC (gradient 25-10% Water/acetonitrile+0.05% trifluoroacetic acid) to yield 2-isoquinolin-3-yl-7-phenylethynyl-chromen-4-one oxime (7.3 mg, 13%) as a yellow solid and a 80/20 mixture of Z/E oxime isomers.

後処理

  1. extractionextracted with ethyl acetate
  2. custompurified by preparative HPLC (gradient 25-10% Water/acetonitrile+0.05% trifluoroacetic acid)

出典と根拠

ORDレコード
ord-637f69a9793e42fd96165286306e7c70
出典データセット
uspto-grants-2015_02
特許番号
US08962627B2

反応ノート

読み込み中…