Hydrochloric Acid → ethyl 4-iodo-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 1752644ノート

反応式

HRID 1752644 の反応式
O[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[N:14]([CH3:17])[CH:15]=[CH:16][C:3]=12.N1C=CC=CC=1.O(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.[Na+].[I-:40].Cl.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(#N)C.C(OCC)(=O)C>[I:40][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[N:14]([CH3:17])[CH:15]=[CH:16][C:3]=12

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 67749Trifluoromethanesulfonic anhydrideHCID 178469181HCID 178469181、化合物

生成物 1

HCID 89923718ethyl 4-iodo-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate収率 100%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

A 0° C. solution of ethyl 4-hydroxy-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (10.0 g, 42.7 mmol) in acetonitrile (200 mL) and pyridine (4.13 mL, 51.2 mmol) was treated dropwise with Tf2O (8.65 mL, 51.2 mmol). After 1 h, the reaction mixture was treated with NaI (19.20 g, 128 mmol) followed by dropwise addition of 3M HCl (17.08 mL, 51.2 mmol) and warmed to 70° C. After 3 h, the reaction mixture was cooled to ambient temperature and added to a sat. aq. solution of Na2S2O3. After stirring for 15 min, ethyl acetate was added and the layers partitioned. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford ethyl 4-iodo-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (14.7 g).

後処理

  1. waitAfter 3 h
  2. temperaturethe reaction mixture was cooled to ambient temperature
  3. customthe layers partitioned
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e24b3608d123461080f3bb1f709871d2
出典データセット
uspto-grants-2015_10
特許番号
US09163023B2

反応ノート

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