Tetrahydrofuran → HCID 57747428, 화합물

HRID 222087노트

반응식

HRID 222087 반응식
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][C:10]2[C:11]3[N:34]([CH3:35])[CH:33]=[CH:32][C:12]=3[N:13]=[C:14]([N:16]([C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[N:15]=2)=[C:4]([CH3:36])[CH:3]=1.[N:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1.C1COCC1.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.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>[CH3:36][C:4]1[CH:3]=[C:2]([C:40]2[CH:41]=[CH:42][N:37]=[CH:38][CH:39]=2)[CH:7]=[C:6]([CH3:8])[C:5]=1[S:9][C:10]1[C:11]2[N:34]([CH3:35])[CH:33]=[CH:32][C:12]=2[N:13]=[C:14]([N:16]([C:24]2[CH:25]=[CH:26][C:27]([C:30]#[N:31])=[CH:28][CH:29]=2)[C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[N:15]=1

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 57747383HCID 57747383, 화합물

생성물 1

HCID 57747428HCID 57747428, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

tert-Butyl 4-(4-bromo-2,6-dimethylphenylthio)-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl(4-cyanophenyl)carbamate (0.729 mmol) is combined with pyridine-4-boronic acid (1.46 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.0729 mmol) in a two dram vial. The vial is sealed and flushed with argon. Degassed THF (5.0 mL) and aqueous Na2CO3 (2 M, 1.5 mL, 3.0 mmol) are injected, and the mixture agitated on a shaker at 80° C. for 10 h. The mixture is diluted with ethyl acetate and extracted with aqueous Na2CO3 (0.5 M, ×2). The organic layer is collected, concentrated, and the residue purified by chromatography (SiO2, 1:4 hexanes/EtOAc).

후처리

  1. customThe vial is sealed
  2. customflushed with argon
  3. extractionextracted with aqueous Na2CO3 (0.5 M, ×2)
  4. customThe organic layer is collected
  5. concentrationconcentrated
  6. customthe residue purified by chromatography (SiO2, 1:4 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-186c07296949493b96c3766341f57f71
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207178B2

반응 노트

불러오는 중…