Sodium Carbonate → tert-Butyl 4-(2-formyl-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)benzoate

HRID 1772710

반응식

HRID 1772710 반응식
Br[C:2]1[N:7]2[CH:8]=[C:9]([CH:11]=[O:12])[N:10]=[C:6]2[C:5]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[N:4][CH:3]=1.[C:19]([O:23][C:24]([C:26]1[CH:31]=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][CH:27]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:11]([C:9]1[N:10]=[C:6]2[C:5]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[N:4][CH:3]=[C:2]([C:29]3[CH:30]=[CH:31][C:26]([C:24]([O:23][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:25])=[CH:27][CH:28]=3)[N:7]2[CH:8]=1)=[O:12]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 43767661,1-Dimethylethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 1177281135-Bromo-8-morpholinoimidazo[1,2-a]pyrazine-2-carbaldehyde

생성물 1

HCID 117733763tert-Butyl 4-(2-formyl-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)benzoate

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

A mixture of compound 2a (1.0 g, 3.2 mmol), 4-(tert-butoxycarbonyl)phenylboronic acid pinacol ester (1.2 g, 3.9 mmol), PdCl2(dppf) (260 mg, 0.30 mmol), 2M Na2CO3 (8.0 mL, 16 mmol) in dioxane (10 mL) was heated to 80° C. for 2 h. The reaction was cooled, filtered through a diatomaceous earth-filled cartridge (2.5 g), and the filter cake was rinsed with EtOAc. The combined filtrates were concentrated under reduced pressure. The residue was diluted with DCM and extracted with water, brine, then dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was triturated with MeOH, filtered and dried to give compound 67a. Mass Spectrum (LCMS, ESI pos.) Calcd. for C22H24N4O4: 409.4 [M+H]. found 409.4.

후처리

  1. temperatureThe reaction was cooled
  2. filtrationfiltered through a diatomaceous earth-filled cartridge (2.5 g)
  3. washthe filter cake was rinsed with EtOAc
  4. concentrationThe combined filtrates were concentrated under reduced pressure
  5. additionThe residue was diluted with DCM
  6. extractionextracted with water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was triturated with MeOH
  11. filtrationfiltered
  12. customdried

출처 및 근거

ORD 기록
ord-d61ac791e301454596f7dfe16c067364
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249163B2

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