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3-Cyano-4-fluorophenylboronic acid → 5-(8-Amino-3-cyclobutylimidazo[1,5-a]pyrazin-1-yl)-2-fluorobenzonitrile

HRID 449073
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HRID 449073 반응식
[CH:1]1([C:5]2[N:9]3[CH:10]=[CH:11][N:12]=[C:13]([NH2:14])[C:8]3=[C:7](I)[N:6]=2)[CH2:4][CH2:3][CH2:2]1.[C:16]([C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][C:23]=1[F:24])#[N:17]>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.COCCOC.O>[NH2:14][C:13]1[C:8]2[N:9]([C:5]([CH:1]3[CH2:4][CH2:3][CH2:2]3)=[N:6][C:7]=2[C:20]2[CH:21]=[CH:22][C:23]([F:24])=[C:18]([CH:19]=2)[C:16]#[N:17])[CH:10]=[CH:11][N:12]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 27579643-Cyano-4-fluorophenylboronic acidHCID 426093653-Cyclobutyl-1-iodoimidazo[1,5-a]pyrazin-8-amine

생성물 1

HCID 669156655-(8-Amino-3-cyclobutylimidazo[1,5-a]pyrazin-1-yl)-2-fluorobenzonitrile

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 18180031Water 1,2-dimethoxyethane용매

실험 절차

Into a 10 mL microwave vessel were added 3-cyclobutyl-1-iodoimidazo[1,5-a]pyrazin-8-amine (100 mg, 0.0003 mol), 3-cyano-4-fluorophenylboronic acid (0.068 g, 0.00041 mol) potassium carbonate (88 mg, 0.00063 mol), Pd(PPh3)4 (40 my, 0.00003 mol), DME/Water (5:1) (5:1, DME:H2O, 1 mL) and the vessel was degassed 3× with N2. The reaction was microwaved on 300 watts, 100° C. for 45 min. The reaction vessel was resubjected to the microwave heating under the same conditions as before for 45 min. Purification by prep TLC using 4% MeOH in DCM eluting twice afforded 54 mg of the title compound as a yellow solid. MS (ES+): m/z 308.11 (100)[MH+]. HPLC: tR=2.14 min (Open Lynx polar—5 min).

후처리

  1. customthe vessel was degassed 3× with N2
  2. customThe reaction was microwaved on 300 watts, 100° C. for 45 min
  3. temperatureheating under the same conditions as before for 45 min
  4. customPurification by prep TLC
  5. customHPLC: tR=2.14 min (Open Lynx polar—5 min)

출처 및 근거

ORD 기록
ord-9851623963ca40159ae6819ebc25e693
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08481733B2

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