Methanol → HCID 18172427, compound

HRID 397100Notes

Reaction equation

HRID 397100 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15]C)[CH:11]=2)[CH:6]1[CH:17]1[CH2:22][CH2:21][N:20]([S:23]([C:26]2[N:27]=[CH:28][N:29]([CH3:31])[CH:30]=2)(=[O:25])=[O:24])[CH2:19][CH2:18]1)=[O:4].B(Br)(Br)Br.CO.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:32][C:2]([F:1])([F:33])[C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:15])[CH:11]=2)[CH:6]1[CH:17]1[CH2:18][CH2:19][N:20]([S:23]([C:26]2[N:27]=[CH:28][N:29]([CH3:31])[CH:30]=2)(=[O:25])=[O:24])[CH2:21][CH2:22]1)=[O:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 18172405HCID 18172405, compound

Product 1

HCID 18172427HCID 18172427, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2,2,2-trifluoro-1-{6-methoxy-1-[1-(1-methyl-1H-imidazole-4-sulfonyl)-piperidin-4-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-ethanone (0.036 g, 0.074 mmol) in CH2Cl2 (3 ml) under an atmosphere of N2 cooled to −78° C. was added boron tribromide as a 1.0 M solution in CH2Cl2 (0.3 ml, 0.3 mmol). The reaction mixture was stirred overnight slowly, while allowing it to warm to RT. MeOH (1 ml) was added to the reaction mixture and stirring was continued at RT for 10 minutes. Sat. NaHCO3 was added to the reaction mixture until the pH of the aqueous layer was 7. The mixture was then extracted with EtOAc (3×20 ml), the combined organics were washed with brine (1×20 ml), dried over MgSO4, filtered, and concentrated in vacuo to give the desired product as an off white solid (0.028 g, 0.059 mmol, 80% yield).

Workup

  1. stirringstirring
  2. waitwas continued at RT for 10 minutes
  3. extractionThe mixture was then extracted with EtOAc (3×20 ml)
  4. washthe combined organics were washed with brine (1×20 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e328663d15fa4420bb481f5ab72e1950
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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