Boron tribromide → HCID 117992578, compound

HRID 717108Notes

Reaction equation

HRID 717108 reaction equation
C[O:2][CH2:3][CH2:4][N:5]([CH2:26][CH2:27][O:28]C)[C:6](=[O:25])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][C:15](=[O:24])[C:16]3[C:21]([CH:22]=2)=[C:20]([CH3:23])[CH:19]=[CH:18][CH:17]=3)=[CH:9][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:28][CH2:27][CH2:26][N:5]([CH2:4][CH2:3][OH:2])[C:6](=[O:25])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][C:15](=[O:24])[C:16]3[C:21]([CH:22]=2)=[C:20]([CH3:23])[CH:19]=[CH:18][CH:17]=3)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 117992760HCID 117992760, compound

Product 1

HCID 117992578HCID 117992578, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N,N-Bis-(2-methoxy-ethyl)-4-(5-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzamide (40 mg, 0.10 mmol) in CH2Cl2 (2.5 mL) under N2 at −78° C. was added boron tribromide (1M in CH2Cl2, 2.54 mL, 2.54 mmol). The reaction was allowed to warm to RT and stirred for 16 h. The reaction mixture was quenched with H2O and extracted with EtOAc (5 mL) upon which a pale yellow solid precipitated and was filtered off. The aqueous phase was further extracted with CH2Cl2 (5 mL). The combined organics were evaporated to dryness. Product was found to be also present in the aqueous phase and was passed through an Isolute-103 cartridge (500 mg), washing with H2O (4× column volumes). The product was eluted from the column with MeOH (4× column volumes) and evaporated to dryness. The combined crude product was purified by reverse phase preparative HPLC-MS to obtain N,N-bis-(2-hydroxy-ethyl)-4-(5-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzamide as a white solid (23 mg, 63%).

Workup

  1. customThe reaction mixture was quenched with H2O
  2. extractionextracted with EtOAc (5 mL) upon which a pale yellow solid
  3. customprecipitated
  4. filtrationwas filtered off
  5. extractionThe aqueous phase was further extracted with CH2Cl2 (5 mL)
  6. customThe combined organics were evaporated to dryness
  7. washwashing with H2O (4× column volumes)
  8. washThe product was eluted from the column with MeOH (4× column volumes)
  9. customevaporated to dryness
  10. customwas purified by reverse phase preparative HPLC-MS

Sources & evidence

ORD record
ord-48aefff018bd4d53a20472c5706e828c
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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