Ethyl Acetate → HCID 86602074, compound

HRID 420632Notes

Reaction equation

HRID 420632 reaction equation
[Cl:1][C:2]1[C:3]([O:32]C)=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[CH:8]([NH:13][C:14]1[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=1[CH:16]=[CH:17][NH:18][C:19]3=[O:24])[C:7]([OH:29])([C:25]([F:28])([F:27])[F:26])[CH2:6][C:5]2([CH3:31])[CH3:30].B(Br)(Br)Br.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>ClCCl>[Cl:1][C:2]1[C:3]([OH:32])=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[CH:8]([NH:13][C:14]1[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=1[CH:16]=[CH:17][NH:18][C:19]3=[O:24])[C:7]([OH:29])([C:25]([F:28])([F:26])[F:27])[CH2:6][C:5]2([CH3:30])[CH3:31]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25134Boron tribromide2×HCID 516892Sodium BicarbonateHCID 66657326HCID 66657326, compound

Product 1

HCID 86602074HCID 86602074, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

40 mg (0.083 mmol) of (rac.) 5-{[6-chloro-2-hydroxy-5-methoxy-4,4,7-trimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-isoquinolin-1(2H)-one is mixed at room temperature with 0.8 ml of a 1 molar solution of boron tribromide in dichloromethane, and it is stirred for four hours at room temperature. Since starting material is still present, another 0.8 ml of boron tribromide solution is added, and it is stirred for 16 hours at room temperature. The reaction mixture is mixed drop by drop with saturated sodium bicarbonate solution (pH 8) at −30° C. The batch is mixed with ethyl acetate, and the cold bath is removed. After 10 minutes of vigorous stirring at room temperature, the batch is extracted twice with ethyl acetate. The organic phases are washed with water and with brine, dried, and the residue is chromatographed on silica gel (mobile solvent methanol/dichloromethane) after the solvent is spun off 19.9 mg (51.2%) of the desired compound is isolated.

Workup

  1. stirringit is stirred for 16 hours at room temperature
  2. customthe cold bath is removed
  3. stirringAfter 10 minutes of vigorous stirring at room temperature
  4. extractionthe batch is extracted twice with ethyl acetate
  5. washThe organic phases are washed with water and with brine
  6. customdried
  7. customthe residue is chromatographed on silica gel (mobile solvent methanol/dichloromethane) after the solvent
  8. customis isolated

Sources & evidence

ORD record
ord-0649296e21d8492b8f124f2fcc62eeac
Source dataset
uspto-grants-2012_01
Patent number
US08097627B2

Reaction notes

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