Triethylamine → HCID 86698827, 화합물

HRID 1054836노트

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HRID 1054836 반응식
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

참가 물질

7

반응물 3

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

생성물 1

HCID 86698827HCID 86698827, 화합물수율 37.9%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
120 °C

실험 절차

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

후처리

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

출처 및 근거

ORD 기록
ord-930ebe6c8c5b4179b4563fd3e8eb3e87
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394285B2

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