Cyclohexanol → HCID 22933374, compound

HRID 1269794Notes

Reaction equation

HRID 1269794 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]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.[NH:49]1[C:57]2[C:52](=[CH:53][C:54](O)=[CH:55][CH:56]=2)[CH:51]=[N:50]1>O1CCCC1>[CH:1]1([O:7][C:54]2[CH:53]=[C:52]3[C:57](=[CH:56][CH:55]=2)[NH:49][N:50]=[CH:51]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 7966CyclohexanolHCID 11776TriphenylphosphineHCID 755571,2-Bis(phenylmethyl) 1,2-diazenedicarboxylateHCID 1014381H-Indazol-5-ol

Product 1

HCID 22933374HCID 22933374, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclohexanol (0.315 ml, 2.98 mmol), triphenylphosphine (442 mg, 1.64 mmol) and dibenzyl azodicarboxylate (534 mg, 1.17 mmol) were added at 0° C. to a solution of the 1H-indazol-5-ol (200 mg, 1.49 mmol) obtained in Reference Example 4 in tetrahydrofuran (16 ml). After 30 minutes, the mixture thus obtained was warmed up to room temperature. After stirring overnight, the reaction solution was concentrated under reduced pressure and a-1M aqueous sodium hydroxide solution (20 ml) was added to the resulting residue, followed by extraction with ethyl acetate (20 ml×2). The organic layer was 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: chloroform/methanol, hexane/ethyl acetate) to obtain 5-(cyclohexyloxy)-1H-indazole (140 mg, 43%).

Workup

  1. customthe mixture thus obtained
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additiona-1M aqueous sodium hydroxide solution (20 ml) was added to the resulting residue
  4. extractionfollowed by extraction with ethyl acetate (20 ml×2)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customThe organic layer dried
  7. concentrationwas concentrated under reduced pressure
  8. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-db86c05c79a34578afa8e4aecaada974
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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