2-Bromo-1-ethylpyridinium tetrafluoroborate → HCID 136359776, compound

HRID 2360693Notes

Reaction equation

HRID 2360693 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([C:25](O)=[O:26])[C:12]2[C:17]([CH3:18])=[N:16][N:15]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[C:13]=2[N:14]=1.F[B-](F)(F)F.BrC1C=CC=C[N+]=1CC.[C:42]([N:49]1[CH2:54][CH2:53][NH:52][C:51]([CH3:56])([CH3:55])[CH2:50]1)([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43]>ClCCl.C(N(CC)C(C)C)(C)C>[C:45]([O:44][C:42]([N:49]1[CH2:54][CH2:53][N:52]([C:25]([C:11]2[C:12]3[C:17]([CH3:18])=[N:16][N:15]([CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][O:20]4)[C:13]=3[N:14]=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([OH:8])=[CH:7][C:2]=3[F:1])[CH:10]=2)=[O:26])[C:51]([CH3:56])([CH3:55])[CH2:50]1)=[O:43])([CH3:48])([CH3:46])[CH3:47]

Participants

6

Reactant 3

HCID 27363002-Bromo-1-ethylpyridinium tetrafluoroborateHCID 227103871-Boc-3,3-dimethylpiperazineHCID 136359777HCID 136359777, compound

Product 1

HCID 136359776HCID 136359776, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a suspension of 6-(2-fluoro-4-Hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (150 mg) in dry dichloromethane (3 mL), N,N-diisopropylethylamine (70 μL), 2-bromo-1-ethylpyridinium tetrafluoroborate (221 mg) and 1-Boc-3,3-dimethylpiperazine (87 mg) were added. The solution was stirred for 30 min. Upon complete conversion, the solution is evaporated in vacuo and 3 mL of 30% sodium methoxide in methanol were added. The mixture was stirred for 30 min, the pH was adjusted to 5 by addition of 2M hydrochloric acid. Ethyl acetate was added and the organic layer was extracted with saturated sodium bicarbonate, 20% aqueous ammonium chloride solution and multiple times with water. The organic layer was dried over sodium sulfate and evaporated to dryness to give 132 mg (58%) of the title compound.

Workup

  1. additionwere added
  2. customUpon complete conversion, the solution is evaporated in vacuo and 3 mL of 30% sodium methoxide in methanol
  3. additionwere added
  4. stirringThe mixture was stirred for 30 min
  5. additionthe pH was adjusted to 5 by addition of 2M hydrochloric acid
  6. additionEthyl acetate was added
  7. extractionthe organic layer was extracted with saturated sodium bicarbonate, 20% aqueous ammonium chloride solution and multiple times with water
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-ac9be34ff3f5433881710c42dff27c81
Source dataset
uspto-grants-2014_04
Patent number
US08686150B2

Reaction notes

Loading…