Triphenylphosphine → 5-{[4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]oxy}-1H-indazole

HRID 1269806

反応式

HRID 1269806 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([OH:10])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:17][CH:18]1[CH2:23][CH2:22][CH:21](O)[CH2:20][CH2:19]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC1C=CC=CC=1)=O)=NC(OCC1C=CC=CC=1)=O>O1CCCC1>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:17][CH:18]1[CH2:19][CH2:20][CH:21]([O:10][C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)[CH2:22][CH2:23]1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 755571,2-Bis(phenylmethyl) 1,2-diazenedicarboxylateHCID 1014381H-Indazol-5-olHCID 118201114-(tetrahydro-2H-pyran-2-yloxy)cyclohexanol

生成物 1

HCID 184472075-{[4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]oxy}-1H-indazole収率 41.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of the 1H-indazol-5-ol (250 mg) obtained in Reference Example 4 in tetrahydrofuran (15 ml) were added 4-(tetrahydro-2H-pyran-2-yloxy)cyclohexanol (373 mg, 1.86 mmol), triphenylphosphine (538 mg, 2.05 mmol) and dibenzyl azodicarboxylate (667 mg, 2.24 mmol) at 0° C. After 1 hour, the mixture thus obtained was heated to room temperature. After stirring overnight, the reaction solution was concentrated under reduced pressure, and a 1M-aqueous sodium hydroxide solution (50 ml) was added to the resulting residue, followed by extraction with chloroform (50 ml×2). The organic layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 5-{[4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]oxy}-1H-indazole (244 mg, 41%).

後処理

  1. customthe mixture thus obtained
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additiona 1M-aqueous sodium hydroxide solution (50 ml) was added to the resulting residue
  4. extractionfollowed by extraction with chloroform (50 ml×2)
  5. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe organic layer dried
  8. concentrationwas concentrated under reduced pressure
  9. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-1ab6c6e29355446d9dc7a5c17230b146
出典データセット
uspto-grants-2007_04
特許番号
US07199147B2

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