Potassium Carbonate → 5-pyridin-3-yl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

HRID 712591ノート

反応式

HRID 712591 の反応式
Br[C:2]1[CH:3]=[C:4]2[CH2:10][CH2:9][NH:8][C:5]2=[N:6][CH:7]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13](B(O)O)[CH:12]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:2]2[CH:3]=[C:4]3[CH2:10][CH2:9][NH:8][C:5]3=[N:6][CH:7]=2)[CH:12]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 219640795-Bromo-2,3-dihydro-7-azaindole

生成物 1

HCID 675706995-pyridin-3-yl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine収率 60.8%

試薬・触媒・溶媒 3

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

5-Bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (500 mg, 2.5 mmol), 3-pyridinyl-boronic acid (370 mg, 3.0 mmol) and K2CO3 (694 mg, 5.0 mmol) are mixed in 6.5 mL of 1,4-dioxane and 0.65 mL of water. Argon gas is bubbled through the mixture for 10 min and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (178 mg, 0.25 mmol) is added. The mixture is heated at 100° C. for 16 hrs. Then the solvents are removed and EtOAc (50 mL) is added along with 30 mL of water. The mixture is filtered to remove any solid and the organic layer is separated. The aqueous layer is extracted with EtOAc (2×25 mL) and the organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 300 mg of 5-pyridin-3-yl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine.

後処理

  1. customArgon gas is bubbled through the mixture for 10 min
  2. customThen the solvents are removed
  3. additionEtOAc (50 mL) is added along with 30 mL of water
  4. filtrationThe mixture is filtered
  5. customto remove any solid
  6. customthe organic layer is separated
  7. extractionThe aqueous layer is extracted with EtOAc (2×25 mL)
  8. concentrationconcentrated
  9. customto give the crude product
  10. customPurification by flash column chromatography

出典と根拠

ORDレコード
ord-3281b763d231458fa7fc0c5c66cb8c03
出典データセット
uspto-grants-2015_11
特許番号
US09181272B2

反応ノート

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