1,2-Dimethoxyethane → HCID 67497023, compound

HRID 1628230Notes

Reaction equation

HRID 1628230 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11](B2OC(C)(C)C(C)(C)O2)=[CH:10][CH:9]=[N:8]1.Br[C:22]1[CH:23]=[C:24]([NH2:30])[C:25]([O:28][CH3:29])=[N:26][CH:27]=1.COCCOC>O>[CH3:29][O:28][C:25]1[C:24]([NH2:30])=[CH:23][C:22]([C:11]2[N:7]([CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)[N:8]=[CH:9][CH:10]=2)=[CH:27][N:26]=1

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 115872081-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 447548695-Bromo-2-methoxypyridin-3-amine

Product 1

HCID 67497023HCID 67497023, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
92 °C

Procedure

To a 100 ml flask was added 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 14.1.B (6.0 g, 22 mmol), 5-bromo-2-methoxypyridin-3-amine (4 g, 20 mmol), 100 ml of DME, and 30 ml of water. Argon was then bubbled through the solution for 8 minutes at which time Pd(Ph3)4 (460 mg, 0.39 mmole) was added and argon was then bubbled through the solution for an additional 2 minutes. The reaction was then heated to 92° C. for 12 hours at which time the crude was quenched with brine and extracted with EtAc. The solvent was removed and the crude purifed on silica gel (eluting with 0-70% EtAc in Hexanes) to 2-methoxy-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)pyridin-3-amine 14.1.C (5.3 g, 97. % yield).

Workup

  1. additionwas added
  2. customargon was then bubbled through the solution for an additional 2 minutes
  3. customwas quenched with brine
  4. extractionextracted with EtAc
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-05459273daaa4922a7ff11eb5d444f26
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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