Triethylamine → HCID 86698827、化合物

HRID 1054836ノート

反応式

HRID 1054836 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][N:6]=[C:5]2[C:12]([O:14][CH3:15])=[O:13].C(N(CC)CC)C.[C:23]1([C:29]#[CH:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu](I)I>[Cl:11][C:10]1[CH:9]=[C:8]2[C:4]([C:5]([C:12]([O:14][CH3:15])=[O:13])=[N:6][NH:7]2)=[CH:3][C:2]=1[C:30]#[C:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 86698828methyl 5-bromo-6-chloro-1H-indazole-3-carboxylate

生成物 1

HCID 86698827HCID 86698827、化合物収率 37.9%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
120 °C

実験手順

A mixture of methyl 5-bromo-6-chloro-1H-indazole-3-carboxylate (50 mg, 0.17 mmol), triethylamine (0.05 mL, 0.4 mmol), tetrakis(triphenylphosphine)palladium(0) (10.7 mg, 0.009 mmol), copper iodide (3.0 mg, 0.017 mmol) and phenyl acetylene (20 mg, 0.20 mmol) in tetrahydrofuran (1.0 mL) was sealed and heated to 120° C. for 16 hours. The cooled reaction mixture was concentrated in vacuo and purified by flash chromatography utilizing heptanes/ethyl acetate (1:1 to 0:1) to give the title compound (20 mg) as a yellow solid. MS (ES−): 309.0 (M−H)− Step 2

後処理

  1. customwas sealed
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated in vacuo
  4. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-930ebe6c8c5b4179b4563fd3e8eb3e87
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

反応ノート

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