Boron tribromide → HCID 136116857, compound

HRID 1808901Notes

Reaction equation

HRID 1808901 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[C:17]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28]C)=[N:18][O:19][C:20]=3[CH3:21])=[O:15])[CH2:10][CH2:9]2)=[CH:6][C:5]([NH:30][C:31](=[O:41])[C:32]2[CH:37]=[CH:36][C:35]([N:38]([CH3:40])[CH3:39])=[CH:34][CH:33]=2)=[C:4]([N+:42]([O-:44])=[O:43])[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[C:17]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[OH:28])=[N:18][O:19][C:20]=3[CH3:21])=[O:15])[CH2:10][CH2:9]2)=[CH:6][C:5]([NH:30][C:31](=[O:41])[C:32]2[CH:37]=[CH:36][C:35]([N:38]([CH3:39])[CH3:40])=[CH:34][CH:33]=2)=[C:4]([N+:42]([O-:44])=[O:43])[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 56925242HCID 56925242, compound

Product 1

HCID 136116857HCID 136116857, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To N-(4-chloro-5-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)-2-nitrophenyl)-4-(dimethylamino)benzamide (Example 14, 50 mg, 0.081 mmol) in 7 mL of DCM at −78° C. was added 0.24 mL of 1.0 M boron tribromide in DCM. The solution was stirred at room temperature for 16 hours. Solvent was evaporated in vacuo and the product was purified by preparative HPLC (acetonitrile/water, 10 mM NH4OAc) to give 42 mg of the title compound. 1H-NMR (CDCl3, 400 MHz): δ 11.52 (1H, s), 8.70 (1H, s), 8.30 (1H, s), 7.90 (2H, d, J=9.0 Hz), 7.45-7.33 (2H, m), 7.15-7.07 (1H, m), 7.04-6.95 (1H, m), 6.88 (2H, d, J=8.8 Hz), 4.07-4.00 (2H, m), 3.38 (4H, s), 3.12 (6H, s), 2.99 (2H, s), 2.57 (3H, s). HPLC/MS (Method G): (ES+) m/z (M+H)+=605; Rt=2.29 min.

Workup

  1. customSolvent was evaporated in vacuo
  2. customthe product was purified by preparative HPLC (acetonitrile/water, 10 mM NH4OAc)

Sources & evidence

ORD record
ord-7c9bebee9b3c48ee9e339abd7237c3ae
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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