Boron tribromide → Methyl 4-{[(4-tert-butylcyclohexyl)(5-hydroxy-1-methyl-1h-benzimidazol-2-yl)amino]methyl}benzoate

HRID 230005Notes

Reaction equation

HRID 230005 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:24][C:25]2[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([O:22]C)=[CH:21][C:14]=3[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([N:11]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:33][CH:34]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:14]=3[N:13]=2)[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 68834931Methyl 4-{[(4-tert-butylcyclohexyl)(5-methoxy-1-methyl-1h-benzimidazol-2-yl)amino]methyl}benzoate

Product 1

HCID 68835422Methyl 4-{[(4-tert-butylcyclohexyl)(5-hydroxy-1-methyl-1h-benzimidazol-2-yl)amino]methyl}benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of the title compound of Example 14 Step C (1 mmol, 464 mg) in 5 mL of DCM at −78° C. under N2 was added dropwise BBr3 (5 mmol, 5 mL of a 1M solution in DCM). The reaction was allowed to warm to ambient temperature. After 15 min the reaction was poured into stirring NaHCO3 (gas evolution), and the product was extracted with DCM. The organic layer was dried with Na2SO4 and concentrated under reduced pressure, affording the product as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.90 (d, 2H), 7.44 (d, 2H), 7.28 (unres. m, 1H), 7.01 (d, 1H), 6.83 (dd, 1H), 4.64 (s, 2H), 3.89 (s, 3H), 3.58 (s, 3H), 3.20 (m, 1H), 2.10 (m, 2H), 1.89 (m, 2H), 1.59 (m, 2H), 0.98-1.14 (overlapping m, 3H), 0.86 (s, 9H). MS (ESI): m/z 450 (M+H). HPLC A: 2.30 min.

Workup

  1. additionAfter 15 min the reaction was poured
  2. extractionthe product was extracted with DCM
  3. dry with materialThe organic layer was dried with Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-533fd74147ce466ba7813568b438e6d8
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Reaction notes

Loading…