Trifluoroacetic acid → 1-benzenesulfonyl-5-chloro-3-(2-methylsulfanyl-pyrimidin-5-ylmethyl)-1H-pyrrolo[2,3-b]pyridine

HRID 509979노트

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HRID 509979 반응식
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Cl:19])[CH:18]=[C:13]3[C:12]([CH:20]([C:22]3[CH:23]=[N:24][C:25]([S:28][CH3:29])=[N:26][CH:27]=3)O)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Cl:19])[CH:18]=[C:13]3[C:12]([CH2:20][C:22]3[CH:23]=[N:24][C:25]([S:28][CH3:29])=[N:26][CH:27]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57619161(1-benzenesulfonyl-5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-(2-methylsulfanyl-pyrimidin-5-yl)-methanol

생성물 1

HCID 576194221-benzenesulfonyl-5-chloro-3-(2-methylsulfanyl-pyrimidin-5-ylmethyl)-1H-pyrrolo[2,3-b]pyridine수율 64.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

To (1-benzenesulfonyl-5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-(2-methylsulfanyl-pyrimidin-5-yl)-methanol (130, 4.70 g, 10.5 mmol) in 120.0 mL of acetonitrile, triethylsilane (22.0 mL, 138 mmol) and trifluoroacetic acid (11.0 mL, 143 mmol) were added. The reaction was stirred at 80° C. for 3 hours, then concentrated under vacuum and mixed with aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 20-100% ethyl acetate in hexane. Appropriate fractions were combined and solvents removed under vacuum to provide the desired compound (131, 2.90 g).

후처리

  1. concentrationconcentrated under vacuum
  2. additionmixed with aqueous potassium carbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe resulting material was purified by silica gel column chromatography
  8. washeluting with 20-100% ethyl acetate in hexane
  9. customsolvents removed under vacuum

출처 및 근거

ORD 기록
ord-db7447f27cb54ed19b856c2ad7090706
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096593B2

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