(Dimethyl sulfide)trihydroboron → HCID 136623244, compound

HRID 2279165Notes

Reaction equation

HRID 2279165 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:17]3[C:31]([CH:32]4[CH2:34][CH2:33]4)=[N:30][N:29]([CH:35]4[CH2:40][CH2:39][CH2:38][CH2:37][O:36]4)[C:18]=3[N:19]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[CH:21]=2)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B.CSC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:16]2[CH:21]=[C:20]([C:22]3[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=3)[N:19]=[C:18]3[N:29]([CH:35]4[CH2:40][CH2:39][CH2:38][CH2:37][O:36]4)[N:30]=[C:31]([CH:32]4[CH2:33][CH2:34]4)[C:17]=23)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 136623177HCID 136623177, compound

Product 1

HCID 136623244HCID 136623244, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 790 mg of 4-[3-cyclopropyl-6-(4-hydroxy-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester in 6 ml of dry THF 11.5 ml of borane-dimethylsulfide complex (1 M in DCM) was added slowly at r.t., and the reaction was heated to reflux for 0.5 h. The reaction was quenched by the addition of 7 ml of methanol, and the solvents were evaporated. The residue was purified by flash chromatography (silica, heptanes/ethyl acetate) yielding 635 mg (82%) of the title compound.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 0.5 h
  3. customThe reaction was quenched by the addition of 7 ml of methanol
  4. customthe solvents were evaporated
  5. customThe residue was purified by flash chromatography (silica, heptanes/ethyl acetate)

Sources & evidence

ORD record
ord-013a6bb8699c41f8b260c53ca21bca7f
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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