(Dimethyl sulfide)trihydroboron → HCID 136623205, compound

HRID 2279097Notes

Reaction equation

HRID 2279097 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][C:12]2([CH2:14][CH2:13]2)[N:11]([C:16]([C:18]2[C:19]3[C:39]([CH3:40])=[N:38][N:37]([CH:41]4[CH2:46][CH2:45][CH2:44][CH2:43][O:42]4)[C:20]=3[N:21]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([O:30]C4CCCCO4)=[CH:26][CH:25]=3)[CH:23]=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[CH2:15][C:12]2([CH2:13][CH2:14]2)[N:11]([CH2:16][C:18]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)[N:21]=[C:20]3[N:37]([CH:41]4[CH2:46][CH2:45][CH2:44][CH2:43][O:42]4)[N:38]=[C:39]([CH3:40])[C:19]=23)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 118059329HCID 118059329, compound

Product 1

HCID 136623205HCID 136623205, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 272 mg of) 4-{3-methyl-1-(tetrahydro-pyran-2-yl)-6-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carbonyl}-4,7-diaza-spiro[2.5]-octane-7-carboxylic acid tert-butyl ester in 4 ml of dry THF 3.5 ml of borane-dimethyl-sulfide complex (1 M in DCM) was added slowly at r.t., and the reaction was heated to reflux for 60 min. The reaction was quenched by the addition of 2.2 ml of methanol, and the solvents were evaporated. The residue was purified by flash chromatography (silica, heptane/EtOAc gradient) to obtain 170 mg (74%) of the title compound.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 60 min
  3. customThe reaction was quenched by the addition of 2.2 ml of methanol
  4. customthe solvents were evaporated
  5. customThe residue was purified by flash chromatography (silica, heptane/EtOAc gradient)

Sources & evidence

ORD record
ord-acf01e4c1f7441448f5c5060f7f244e2
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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