Boron tribromide → HCID 178432959, compound

HRID 877389Notes

Reaction equation

HRID 877389 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][CH:14]([C:21]3[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=3)[C:15]3[N:16]=[C:17]([CH3:20])[NH:18][CH:19]=3)=[O:12])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.B(Br)(Br)Br>C(Cl)Cl>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([CH2:10][C:11]([NH:13][CH:14]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)[C:15]3[N:16]=[C:17]([CH3:20])[NH:18][CH:19]=3)=[O:12])=[CH:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178491178HCID 178491178, compound

Product 1

HCID 178432959HCID 178432959, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a 10 ml round bottom flask containing −78° C. solution of 2-(4-cyclopropylphenyl)-N-[(4-methoxyphenyl)(2-methyl-1H-imidazol-4-yl)methyl]acetamide (80.00 mg, 0.213 mmol) in 2.0 ml of CH2Cl2 was added drop-wise 1.0 N BBr3 in CH2Cl2 (1.065 ml, 1.065 mmol). The resulting solution was stirred at −10° C. for 2 hours. The reaction mixture was quenched with diethyl ether. Water was added and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuum. Purification by preparative HPLC (10-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column) to afford 15.20 mg (20%) of the title compound. 1H NMR (CD3OD, 400 MHz) δ 7.136 (m, 4H), 7.012 (m, 2H), 6.938 (d, J=1.10 Hz, 1H), 6.797 (m, 2H), 6.067 (s, 1H), 3.523 (s, 2H), 3.344 (s, 1H), 2.552 (s, 3H), 1.868 (m, 1H), 0.932 (m, 2H), 0.635 (m, 2H). ES-MS [M+1]+: 362.3.

Workup

  1. customThe reaction mixture was quenched with diethyl ether
  2. additionWater was added
  3. extractionextracted with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuum
  8. customPurification
  9. additionby preparative HPLC (10-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column)

Sources & evidence

ORD record
ord-a433208490514065b1e4b5e376ea3c27
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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