Lithium Hexamethyldisilazide → 9-Benzenesulfonyl-5-hydroxy-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 1505849노트

반응식

HRID 1505849 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CO[C:13]([C:15]1[C:23]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[N:17]([S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])[C:16]=1[CH2:33][N:34]([CH2:45][C:46]#[N:47])S(C1C=CC(C)=CC=1)(=O)=O)=[O:14]>C1COCC1>[C:27]1([S:24]([N:17]2[C:16]3[CH:33]=[N:34][C:45]([C:46]#[N:47])=[C:13]([OH:14])[C:15]=3[C:23]3[CH:22]=[CH:21][CH:20]=[N:19][C:18]2=3)(=[O:25])=[O:26])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

참가 물질

4

반응물 2

HCID 2733832Lithium HexamethyldisilazideHCID 582667731-benzenesulfonyl-2-{[cyanomethyl(toluene-4-sulfonyl)amino]methyl}-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester

생성물 1

HCID 582663029-Benzenesulfonyl-5-hydroxy-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-30 °C

실험 절차

Lithium bis(trimethylsilyl)amide (9.6 mL, 1N solution in THF, 9.60 mmol) was added dropwise to a cooled (−78° C.) suspension of 1-benzenesulfonyl-2-{[cyanomethyl(toluene-4-sulfonyl)amino]methyl}-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (1.72 g, 3.19 mmol) in dry THF (50 mL). The reaction mixture was allowed to warm to −30° C., stirred at −30° C. for 2 h, before warming to ambient temperature. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (30 mL) and water (50 mL). The aqueous phase was extracted with DCM (2×20 mL) and the combined organic phase was washed with brine and concentrated in vacuo. The resultant solid was triturated with THF (2×4 mL) to afford the title compound. The filtrate was purified by flash chromatography (silica, 5 g column, Si-SPE, ethyl acetate then 10-20% MeOH in DCM) to afford the remaining title compound. The two batches of material were combined to afford a yellow solid (1.03 g, 90%). LCMS (Method B): RT=3.26 min, M+H+=351.

후처리

  1. temperaturea cooled
  2. temperaturebefore warming to ambient temperature
  3. customThe reaction mixture was quenched with saturated aqueous ammonium chloride solution (30 mL) and water (50 mL)
  4. extractionThe aqueous phase was extracted with DCM (2×20 mL)
  5. washthe combined organic phase was washed with brine
  6. concentrationconcentrated in vacuo
  7. customThe resultant solid was triturated with THF (2×4 mL)

출처 및 근거

ORD 기록
ord-31dd8f1e93494d85b0b02cb222a75b28
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216980B2

반응 노트

불러오는 중…