4-(Hydroxymethyl)benzeneboronic acid → HCID 86653489, 화합물

HRID 1888376노트

반응식

HRID 1888376 반응식
Br[C:2]1[CH:24]=[N:23][C:5]2[N:6]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:7]3[CH:12]=[N:11][C:10]([C:13]#[N:14])=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[OH:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1>C(#N)C.[F-].[K+].O>[OH:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:24]2[CH:2]=[CH:3][C:4]3[C:8]4[CH:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=4[N:6]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:5]=3[N:23]=2)=[CH:29][CH:28]=1

참가 물질

6

반응물 2

HCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 58266568HCID 58266568, 화합물

생성물 1

HCID 86653489HCID 86653489, 화합물수율 172.5%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 522689Potassium Fluoride용매

반응 조건

온도
140 °C

실험 절차

A mixture of 3-bromo-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (700 mg, 0.87 mmol), 4-hydroxymethylbenzeneboronic acid (400 mg, 1.32 mmol) and 1,1′-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) (52.5 mg, 0.064 mmol) in acetonitrile (21 mL) and 2N aqueous potassium fluoride solution (21 mL) was devided equally across two 25 mL microwave vials. Each vial was degassed with nitrogen for 10 minutes before the mixtures were heated under microwave irradiation at 140° C. for 30 minutes. The reaction mixtures were allowed to cool to ambient temperature, combined and diluted with water (50 mL). The precipitate was collected by filtration, washed with water (50 mL) and left to air dry. The resultant grey solid was purified by flash column chromatography (silica, 40 g column, ISCO, 0-100% ethyl acetate in cyclohexane). The isolated solid was then triturated with hot t-BME to afford the title compound as a light grey solid (646 mg, 26%). LCMS (Method B): RT=4.11 min, M+H+=431.

후처리

  1. customEach vial was degassed with nitrogen for 10 minutes before the mixtures
  2. customThe reaction mixtures
  3. temperatureto cool to ambient temperature
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water (50 mL)
  6. waitleft to air
  7. customdry
  8. customThe resultant grey solid was purified by flash column chromatography (silica, 40 g column, ISCO, 0-100% ethyl acetate in cyclohexane)
  9. customThe isolated solid was then triturated with hot t-BME

출처 및 근거

ORD 기록
ord-e158a64d2afd46b39267764c0a8701c9
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501765B2

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