Water → HCID 25123527, compound

HRID 389301Notes

Reaction equation

HRID 389301 reaction equation
[CH2:1]([C:3]1[C:7]([CH2:8][C:9]2[CH:17]=[C:16]([CH3:18])[C:15]([O:19]C)=[C:14]3[C:10]=2[CH2:11][CH2:12][CH2:13]3)=[C:6]([CH2:21][CH3:22])[N:5]([CH2:23][C:24]([OH:26])=[O:25])[N:4]=1)[CH3:2].B(Br)(Br)Br.O>C(Cl)Cl>[CH2:1]([C:3]1[C:7]([CH2:8][C:9]2[CH:17]=[C:16]([CH3:18])[C:15]([OH:19])=[C:14]3[C:10]=2[CH2:11][CH2:12][CH2:13]3)=[C:6]([CH2:21][CH3:22])[N:5]([CH2:23][C:24]([OH:26])=[O:25])[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 66812659HCID 66812659, compound

Product 1

HCID 25123527HCID 25123527, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred suspension of [3,5-Diethyl-4-(7-methoxy-6-methyl-indan-4-ylmethyl)-pyrazol-1-yl]-acetic acid (6.0 gm, 0.0168 mole) in Methylene chloride (100 ml), a solution of Boron tribromide (4.2 ml, 0.0442 mole) in Methylene chloride (20 ml) was added at 0-5° C. and stirred for 2-3 hrs at 20-30° C. Water (250 ml) was charged into the reaction mixture and stirred for 1 hour. The separated solid was filtered under vacuum, washed with water. The obtained solid was dissolved in Ethyl acetate (2.0 liter) and washed with water (1 liter). Ethyl acetate was distilled under vacuum and further the obtained solid was stirred in Diethyl ether (50 ml), filtered and dried at 55-60° C. under vacuum to yield 4.5 gm of desired product.

Workup

  1. stirringstirred for 1 hour
  2. filtrationThe separated solid was filtered under vacuum
  3. washwashed with water
  4. dissolutionThe obtained solid was dissolved in Ethyl acetate (2.0 liter)
  5. washwashed with water (1 liter)
  6. distillationEthyl acetate was distilled under vacuum
  7. stirringfurther the obtained solid was stirred in Diethyl ether (50 ml)
  8. filtrationfiltered
  9. customdried at 55-60° C. under vacuum

Sources & evidence

ORD record
ord-7c02ac7a597346e6ae39db1e712f6f0c
Source dataset
uspto-grants-2013_02
Patent number
US08378118B2

Reaction notes

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