Methanol → 3-Phenyl-5-(phenylmethoxy)-1H-indazole

HRID 1349588Notes

Reaction equation

HRID 1349588 reaction equation
[C:1]1([C:7]([C:9]2[CH:14]=[C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:12]=[CH:11][C:10]=2[NH2:23])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:24]([O-])=O.[Na+].CO.[Sn](Cl)Cl>Cl.O.C1COCC1>[C:1]1([C:7]2[C:9]3[C:10](=[CH:11][CH:12]=[C:13]([O:15][CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:14]=3)[NH:23][N:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 24479Stannous ChlorideHCID 23668193Sodium NitriteHCID 57440914HCID 57440914, compound

Product 1

HCID 224799253-Phenyl-5-(phenylmethoxy)-1H-indazoleYield 48%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-5-(phenylmethoxy)phenyl phenyl ketone (2.6 g, 8.0 mmol) in 6N HCl (70 mL) at 0° C. was added a solution of sodium nitrite (NaNO2) (650 mg, 9.4 mmol) in water (2 mL). To this solution was added methanol and THF to keep it homogeneous. A solution of tin (II) chloride (SnCl2) (5.3 g, 23.6 mmol) in concentrated HCl (20 mL) was then added. The solution was stirred at room temperature overnight. The solid was then filtered and the solution concentrated and chromatographed on silica gel eluting with 20% ethyl acetate in hexane to give the title compound (1.15 g, 48% yield). 1H NMR (DMSO-d6) δ 13.1 (s, 1H), 7.95 (d, 2H), 7.56–7.48 (m, 6H), 7.44–7.3 (m, 4H), 7.14 (d, 1H), 5.12 (s, 2H); ES-MS (m/z) 301 [M+1]+.

Workup

  1. filtrationThe solid was then filtered
  2. concentrationthe solution concentrated
  3. customchromatographed on silica gel eluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-23954ed527f446e29206ebc815d85549
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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