Water → HCID 135804663, compound

HRID 2064604Notes

Reaction equation

HRID 2064604 reaction equation
[CH3:1][C:2]1[C:21]([CH3:22])=[CH:20][C:5]2[NH:6][C:7]([C:9]3[C:17]4[C:12](=[CH:13][CH:14]=[C:15]([O:18]C)[CH:16]=4)[NH:11][N:10]=3)=[N:8][C:4]=2[CH:3]=1.B(Br)(Br)Br.O.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][C:2]1[C:21]([CH3:22])=[CH:20][C:5]2[NH:6][C:7]([C:9]3[C:17]4[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=4)[NH:11][N:10]=3)=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 135900316HCID 135900316, compound

Product 1

HCID 135804663HCID 135804663, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-5-methoxy-1H-indazole [34 mg, Example 235(b)] at 0° C. was treated with a solution of boron tribromide in dichloromethane (0.30 mL, 1M). The mixture was then heated at reflux temperature for 4 hours, then cooled and then treated dropwise with water. The pH was adjusted to between 7 and 8 by the addition of saturated aqueous sodium bicarbonate solution and this mixture was then extracted twice with ethyl acetate. The combined extracts were washed with brine, then dried over magnesium sulfate and then evaporated. The pale yellow solid residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and triethylamine (99:1, v/v) to yield 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1H-indazol-5-ol (23 mg) as a white solid. LC-MS (METHOD B): RT=2.19 minutes; 279 (M+H)+.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux temperature for 4 hours
  3. temperaturecooled
  4. extractionthis mixture was then extracted twice with ethyl acetate
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. additionThe pale yellow solid residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and triethylamine (99:1

Sources & evidence

ORD record
ord-a872af5e2fc6464fad9888307cfb5ee2
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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