Water → 6-Bromo-2-chlorothiazolo[4,5-b]pyridine hydrochloride

HRID 1429536ノート

反応式

HRID 1429536 の反応式
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[C:10]([S-:15])(=S)OCC.[K+].S(Cl)([Cl:20])(=O)=O.O>CN(C=O)C.Cl>[ClH:20].[Br:8][C:6]1[CH:7]=[C:2]2[S:15][C:10]([Cl:20])=[N:9][C:3]2=[N:4][CH:5]=1

参加物

7

反応物 4

HCID 962WaterHCID 24648Sulfuryl chloride2 回HCID 988513,5-Dibromo-2-pyridylamineHCID 2735045Potassium ethylxanthate

生成物 1

HCID 674627556-Bromo-2-chlorothiazolo[4,5-b]pyridine hydrochloride収率 99%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 3,5-dibromopyridine-2-amine (5 g, 19.85 mmol) and potassium O-ethyl carbonodithioate (7.64 g, 47.6 mmol) in DMF (25.6 mL) was heated to 130° C. where it stirred overnight. After this time, the reaction mixture was allowed to cool to rt. Once at the prescribed temperature, the reaction mixture was diluted with HCl (1 N, 150 mL), and then stirred at rt for an additional hour. At the conclusion of this period, the resulting solid was collected by filtration, washed with water (2×15 mL), and then air-dried. The resulting material was suspended in CH2Cl2 (26 mL) and sulfuryl chloride (17.1 mL, 210 mmol) was slowly added. After 2 hr, water (50 mL) was slowly added to decompose the excess sulfuryl chloride (cooled to 0° C.). The resulting precipitate was collected by filtration and dried to afford Compound 21A as a light yellow solid (5.6 g, 99% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.88 (d, J=2.2 Hz, 1H), 8.79 (d, J=2.2 Hz, 1H). LC/MS (m/z)=250 (M+H)+.

後処理

  1. stirringstirred at rt for an additional hour
  2. filtrationAt the conclusion of this period, the resulting solid was collected by filtration
  3. washwashed with water (2×15 mL)
  4. customair-dried
  5. waitAfter 2 hr
  6. filtrationThe resulting precipitate was collected by filtration
  7. customdried

出典と根拠

ORDレコード
ord-49f856b585334548b5a7888eb14bee13
出典データセット
uspto-grants-2015_01
特許番号
US08940716B2

反応ノート

読み込み中…