Lithium Chloride → 5-Bromo-3-furan-3-yl-2-trimethylsilanyl-1H-pyrrolo[2,3-b]pyridine

HRID 2114038ノート

反応式

HRID 2114038 の反応式
[Br:1][C:2]1[CH:3]=[C:4](I)[C:5]([NH2:8])=[N:6][CH:7]=1.[O:10]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][Si:17]([CH3:20])([CH3:19])[CH3:18])=[CH:11]1.[Li+].[Cl-].CC([O-])=O.[K+]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:1][C:2]1[CH:3]=[C:4]2[C:15]([C:12]3[CH:13]=[CH:14][O:10][CH:11]=3)=[C:16]([Si:17]([CH3:18])([CH3:20])[CH3:19])[NH:8][C:5]2=[N:6][CH:7]=1

参加物

7

反応物 4

HCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 15165082-Amino-5-bromo-3-iodopyridineHCID 16217672[2-(Furan-3-yl)ethynyl]trimethylsilane

生成物 1

HCID 598118725-Bromo-3-furan-3-yl-2-trimethylsilanyl-1H-pyrrolo[2,3-b]pyridine収率 22.1%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

実験手順

5-Bromo-3-iodo-pyridin-2-ylamine (12) (390 mg, 1.32 mmol; prepared according to WO0196308), crude acetylene 11 (910 mg), LiCl (56 mg, 1.32 mmol), KOAc (259 mg, 2.64 mmol), Pd(OAc)2 (7.4 mg, 0.03 mmol) in DMF (10 mL) were heated in a sealed tube at 100° C. After 19 h the mixture was partitioned between Et2O and saturated aqueous NH4Cl. The organic layer was separated and the aqueous layer was extracted with Et2O (4×). The combined organic solutions were dried (MgSO4) and concentrated. The residual red oil was purified by PTLC with AcOEt:hexane=1:4 as eluent to yield azaindole 13 (97.9 mg, 22%) as an oil. 1H NMR (400 MHz; CDCl3) δ 0.32 (s, 9H), 6.53 (d, J=0.9 Hz, 1H), 7.51 (s, 1H), 7.55 (t, J=1.6 Hz, 1H), 7.97 (d, J=1.9 Hz, 1H), 8.34 (d, J=2.1 Hz, 1H), 9.09 (brs, NH).

後処理

  1. customAfter 19 h the mixture was partitioned between Et2O and saturated aqueous NH4Cl
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with Et2O (4×)
  4. dry with materialThe combined organic solutions were dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residual red oil was purified by PTLC with AcOEt

出典と根拠

ORDレコード
ord-d6b15e609b524d529ed8ac28eb6a95da
出典データセット
uspto-grants-2008_10
特許番号
US07432375B2

反応ノート

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