Methanol → HCID 135910366, compound

HRID 2423105Notes

Reaction equation

HRID 2423105 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]3[CH:16]=[CH:15][C:14]([O:17]CC4C=CC=CC=4)=[C:13]([F:25])[CH:12]=3)[N:6]=[CH:5][C:4]=2[C:3]=1[OH:26].B(Br)(Br)Br.CO.C([O-])(O)=O.[Na+]>ClCCl.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:25])[CH:12]=3)[N:6]=[CH:5][C:4]=2[C:3]=1[OH:26]

Participants

7

Reactant 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 136085241HCID 136085241, compound

Product 1

HCID 135910366HCID 135910366, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 5-chloro-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-1H-indazol-4-ol (D24) (0.072 g, 0.2 mmol) in dichloromethane (4 mL) was cooled to −78° C. and boron tribromide (0.4 mL of 1M solution in dichloromethane, 0.4 mmol) was added dropwise over 5 mins. After stirring at −78° C. for 3 hrs under argon, methanol (1 mL) was added and the mixture was diluted with dichloromethane (30 mL) and water (30 mL). The pH was adjusted to 7 with NaHCO3 solution and the aqueous layer was separated and extracted with ethyl acetate (35 mL×2). The combined extracts were washed with brine (25 mL), and evaporated. The product was purified by MDAP to give the title compound (E12) as a white solid (0.022 g).

Workup

  1. customthe aqueous layer was separated
  2. extractionextracted with ethyl acetate (35 mL×2)
  3. washThe combined extracts were washed with brine (25 mL)
  4. customevaporated
  5. customThe product was purified by MDAP

Sources & evidence

ORD record
ord-79e01176af7a422c91642704201c4aa3
Source dataset
uspto-grants-2011_06
Patent number
US07960563B2

Reaction notes

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