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

HRID 2059526
ノート
印刷プレビュー

反応式

HRID 2059526 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-63aa036c68ed4cfa95ac2c45576f4991
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08277777B2

反応ノート

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