Cyanogen Bromide → HCID 21111523, compound

HRID 1766819Notes

Reaction equation

HRID 1766819 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([C:15]([NH:17][NH2:18])=[O:16])=[CH:13][N:12]3[CH:19]=[CH:20][N:21]=[C:11]3[C:10]=2[Cl:22])=[C:4]([F:23])[CH:3]=1.[N:24]#[C:25]Br.C(=O)(O)[O-].[Na+]>O1CCOCC1.O.C(OCC)(=O)C>[NH2:24][C:25]1[O:16][C:15]([C:14]2[C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=3[F:23])=[C:10]([Cl:22])[C:11]3[N:12]([CH:19]=[CH:20][N:21]=3)[CH:13]=2)=[N:17][N:18]=1

Participants

7

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 58886642HCID 58886642, compound

Product 1

HCID 21111523HCID 21111523, compoundYield 91.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

7-(4-Bromo-2-fluoro-phenylamino)-8-chloro-imidazo[1,2-a]pyridine-6-carboxylic acid hydrazide (100 mg, 0.25 mmol) was suspended in dioxane (2 mL). Cyanogen bromide (27 mg, 0.253 mmol) was added, followed by a solution of sodium bicarbonate (21 mg, 0.25 mmol) in H2O (1.2 mL). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate and washed with water and saturated aqueous NaCl, dried over Na2SO4 and concentrated to yield the desired product (97 mg, 91%) as a white solid. MS ESI (+) m/z 423, 425 (M+, Cl, Br pattern) detected. 1H NMR (400 MHz, CH3OD) δ 8.98 (s, 1H), 7.95 (s, 1H), 7.61 (s, 1H), 7.33 (d, 1H), 7.17 (d, 1H), 6.78 (t, 1H). 19F (376 MHz, CD3OD) −128.6 (t).

Workup

  1. washwashed with water and saturated aqueous NaCl
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-55b7174c19b14e1294fb79fb392a6dd9
Source dataset
uspto-grants-2007_06
Patent number
US07230099B2

Reaction notes

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