Boron tribromide → HCID 58763648, compound

HRID 2110174Notes

Reaction equation

HRID 2110174 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 with 0.56 ml of boron tribromide (1 mol in methylene chloride) under argon and in a moisture-free environment at −78° C. It is stirred for 15 more minutes, the cold bath is removed, and then it is stirred for another 2 hours. Then, it is mixed with water, the methylene chloride is drawn off, it is made alkaline with sodium bicarbonate solution, and it is extracted twice with 15 ml of ethyl acetate each. 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. customat −78° C
  2. customthe cold bath is removed
  3. stirringit is stirred for another 2 hours
  4. additionThen, it is mixed with water
  5. extractionis extracted twice with 15 ml of ethyl acetate each
  6. customThe collected organic phase is dried
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. customThe residue is chromatographed on silica gel with a gradient of methylene chloride

Sources & evidence

ORD record
ord-acdf6956087d40c99c400ce879f4b7fa
Source dataset
uspto-grants-2009_04
Patent number
US07517894B2

Reaction notes

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