1,2-Dimethoxyethane → 5-(1H-indol-5-yl)-pyrazin-2-ylamine

HRID 719996노트

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HRID 719996 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][C:6](B(O)O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH2:13][C:14]1[CH:19]=[N:18][C:17](Br)=[CH:16][N:15]=1.C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC>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.O>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:17]3[N:18]=[CH:19][C:14]([NH2:13])=[N:15][CH:16]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 5995392-Amino-5-bromopyrazineHCID 27343615-Indolylboronic acid

생성물 1

HCID 218972605-(1H-indol-5-yl)-pyrazin-2-ylamine수율 41.2%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매2회

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온도
90 °C

실험 절차

Nitrogen was bubbled through a solution of 5-indolylboronic acid (340 mg, 2.11 mmol), 2-amino-5-bromopyrazine (245 mg, 1.41 mmol), sodium carbonate (493 mg, 4.65 mmol), dimethoxyethane (12 mL), and water (4 mL) for 15 min. After this time, the solution was treated with dichlorobis(triphenylphosphine)palladium(II) (98 mg, 0.14 mmol), and the resulting reaction mixture was heated at 90° C. for 2 d. The reaction was then poured into water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 35/65 hexanes/ethyl acetate) afforded 5-(1H-indol-5-yl)-pyrazin-2-ylamine (122 mg, 41%) as a brown solid: EI-HRMS m/e calcd for C2H10N4 (M+) 210.0905, found 210.0901.

후처리

  1. customthe resulting reaction mixture
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d5a267116bb14060ac43d0c83651afc1
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132425B2

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