Boron tribromide → HCID 58763648, compound

HRID 858941Notes

Reaction equation

HRID 858941 reaction equation
C[O:2][CH2:3][CH2:4][N:5]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([NH:14][C:15](=[O:35])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[NH:22][CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][C:31]([NH:33][CH3:34])=[O:32])[CH:25]=3)=[CH:11]2)=[N:6]1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][CH2:3][CH2:4][N:5]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([NH:14][C:15](=[O:35])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[NH:22][CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][C:31]([NH:33][CH3:34])=[O:32])[CH:25]=3)=[CH:11]2)=[N:6]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68820057HCID 68820057, compound

Product 1

HCID 58763648HCID 58763648, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 mg (0.11 mmol) of N-[2-(2-methoxy-ethyl)-2H-indazol-5-yl]-2-{[2-(3-methyl-ureido)-pyridin-4-ylmethyl]-amino}-benzamide is introduced into 5 ml of methylene chloride and mixed drop by drop under argon and in a moisture-free environment at −78° C. with 0.56 ml of boron tribromide (1 molar in methylene chloride). It is stirred for 15 more minutes, the cold bath is removed, and it then is stirred for 2 more hours. Then, it is mixed with water, the methylene chloride is drawn off, made alkaline with sodium bicarbonate solution and extracted twice with 15 ml each of ethyl acetate. The collected organic phase is dried, filtered, and concentrated by evaporation. The residue is chromatographed on silica gel with a gradient of methylene chloride:ethanol=100:0 to 90:10 as an eluant, and 27 mg of N-[2-(2-hydroxy-ethyl)-2H-indazol-5-yl]-2-{[2-(3-methyl-ureido)-pyridin-4-ylmethyl]-amino}-benzamide is obtained.

Workup

  1. additionmixed drop by drop under argon
  2. customat −78° C.
  3. customthe cold bath is removed
  4. stirringit then is stirred for 2 more hours
  5. additionThen, it is mixed with water
  6. extractionextracted twice with 15 ml each of ethyl acetate
  7. customThe collected organic phase is dried
  8. filtrationfiltered
  9. concentrationconcentrated by evaporation
  10. customThe residue is chromatographed on silica gel with a gradient of methylene chloride

Sources & evidence

ORD record
ord-38fa3f5dc4c0477ca30c2a7f449e33fe
Source dataset
uspto-grants-2006_12
Patent number
US07148357B2

Reaction notes

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