Acetonitrile → 4-chloro-6-(6-methyl-pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 1878613노트

반응식

HRID 1878613 반응식
Br[C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[C:4]([Cl:11])[CH:3]=1.[CH3:12][C:13]#[N:14]>CC1C=CC=C([Sn](CCCC)(CCCC)CCCC)N=1.C(OCC)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>[Cl:11][C:4]1[CH:3]=[C:2]([C:13]2[CH:12]=[CH:2][CH:3]=[C:4]([CH3:5])[N:14]=2)[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]=12

참가 물질

6

반응물 2

HCID 6342AcetonitrileHCID 247295876-Bromo-4-chloro-1H-pyrrolo[2,3-B]pyridine

생성물 1

HCID 687902414-chloro-6-(6-methyl-pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 3283Diethyl Ether용매HCID 114631832-Methyl-6-(tributylstannyl)pyridine용매

실험 절차

To a solution of 6-bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (1 eq, 11.0 mmol, 2.76 g) in MeCN (20 ml), 2-methyl-6-tributylstannanyl-pyridine (see Chemistry, A European Journal (2005), 11 (23), 6818-6828) (1 eq, 11.0 mmol, 4.19 g) and Pd(PPh3)4 (0.01 eq, 0.110 mmol, 131 mg) are added. The resulting mixture is heated using microwave radiation for 15 min at 160° C. The mixture is diluted with diethyl ether and extracted with aqueous HCl solution (2 M). The aqueous layer is basified with aqueous NaOH solution (4 M) and extracted with DCM. The organic layer is dried with MgSO4, filtered, and concentrated. The residue is taken up in hexane and stirred at r.t. for 1 h. The suspension is filtered and dried giving the title compound; [M+H]+=244.

후처리

  1. temperatureThe resulting mixture is heated
  2. customfor 15 min
  3. customat 160° C
  4. extractionextracted with aqueous HCl solution (2 M)
  5. extractionextracted with DCM
  6. dry with materialThe organic layer is dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. filtrationThe suspension is filtered
  10. customdried

출처 및 근거

ORD 기록
ord-fe753493e87047c18640a683fc65b60f
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314112B2

반응 노트

불러오는 중…