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

HRID 1878613ノート

反応式

HRID 1878613 の反応式
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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 3283Diethyl Ether溶媒HCID 114631832-Methyl-6-(tributylstannyl)pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fe753493e87047c18640a683fc65b60f
出典データセット
uspto-grants-2012_11
特許番号
US08314112B2

反応ノート

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