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Triphenylphosphine → 6-Methoxy-2-[4'-(3''-p-toluenesulfonyloxypropoxy)phenyl]imidazo[1,2-a]pyridine

HRID 2059526
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HRID 2059526 반응식
[C:1]1([CH3:15])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH2:11][CH2:12][CH2:13][OH:14])(=[O:9])=[O:8])=[CH:3][CH:2]=1.O[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:24]=[C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][N:26]3[CH:33]=2)=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1.CN(C)C=O>[CH3:32][O:31][C:28]1[CH:29]=[CH:30][C:25]2[N:26]([CH:33]=[C:23]([C:20]3[CH:19]=[CH:18][C:17]([O:14][CH2:13][CH2:12][CH2:11][O:10][S:7]([C:4]4[CH:3]=[CH:2][C:1]([CH3:15])=[CH:6][CH:5]=4)(=[O:8])=[O:9])=[CH:22][CH:21]=3)[N:24]=2)[CH:27]=1
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참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 3982884-(6-Methoxyimidazo[1,2-a]pyridin-2-yl)phenolHCID 5363146Diisopropyl azodicarboxylateHCID 119613563-Hydroxypropyl 4-methylbenzenesulfonate

생성물 1

HCID 248217926-Methoxy-2-[4'-(3''-p-toluenesulfonyloxypropoxy)phenyl]imidazo[1,2-a]pyridine수율 45.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 554 mg (corresponding to 2.40 mmol) of 1,3-propanediol mono-p-toluenesulfonate in 10 mL of tetrahydrofuran, 260 mg (corresponding to 1.08 mmol) of 2-(4′-hydroxyphenyl)-6-methoxyimidazo[1,2-a]pyridine and 636 mg (corresponding to 2.42 mmol) of triphenylphosphine were added. Further, 5 mL of N,N-dimethylformamide was added thereto to completely dissolve the contents. To the reaction mixture, 0.48 mL (corresponding to 2.42 mmol) of diisopropylazodicarboxylate was added. After the resulting mixture was stirred at room temperature for 23 hours, the reaction solution was concentrated. The resulting crude product was purified by flash silica gel column chromatography (elution solvent: chloroform/ethyl acetate=19/1), further purified by recycle preparative HPLC (HPLC apparatus: LC-908 (under trade name: manufactured by Japan Analytical Industry Co., Ltd.); column: two of JAIGEL 2H (under trade name; manufactured by Japan Analytical Industry Co., Ltd.) connected together; mobile phase: chloroform), and further purified again by flash silica gel column chromatography (elution solvent: hexane/ethyl acetate=35/65) to obtain 220 mg (corresponding to 0.487 mmol) of 6-methoxy-2-[4′-(3″-p-toluenesulfonyloxypropoxy)phenyl]imidazo[1,2-a]pyridine (FIG. 1, Step 7).

후처리

  1. dissolutionto completely dissolve the contents
  2. concentrationthe reaction solution was concentrated
  3. customThe resulting crude product was purified by flash silica gel column chromatography (elution solvent: chloroform/ethyl acetate=19/1)
  4. customfurther purified by recycle preparative HPLC (HPLC apparatus
  5. custommobile phase: chloroform), and further purified again by flash silica gel column chromatography (elution solvent: hexane/ethyl acetate=35/65)

출처 및 근거

ORD 기록
ord-63aa036c68ed4cfa95ac2c45576f4991
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08277777B2

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