Water → HCID 86689810, compound

HRID 1396485Notes

Reaction equation

HRID 1396485 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH2:10])=[N:6][C:7]=1[O:8][CH3:9].[CH3:11][C:12]1(C)[C:16](C)(C)OB(C(C)=C)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CC(N(C)C)=O.CCOC(C)=O.CCOCC>[CH3:9][O:8][C:7]1[N:6]=[C:5]([NH2:10])[CH:4]=[CH:3][C:2]=1[C:12]([CH3:16])=[CH2:11]

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 534202055-Bromo-6-methoxypyridin-2-amine

Product 1

HCID 86689810HCID 86689810, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution 5-bromo-6-methoxypyridin-2-amine (1.72 g, 8.47 mmol) in dimethylacetamide (26 mL) was added 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (2.07 mL, 11.0 mmol), palladium tetrakis(triphenylphoshine) (979 mg, 847 μmol) and tribasic potassium phosphate (3.6 g, 16.9 mmol) in water (7.63 mL, 424 mmol). The mixture was sealed in a microwave vial and heated at 150° C. in a microwave for 15 min. Upon cooling, the mixture was diluted with EtOAc and Et2O, washed with water and brine, concentrated on to silica gel, and chromatographed (10% to 40% EtOAc in hexanes) to give 6-methoxy-5-(prop-1-en-2-yl)pyridin-2-amine contaminated with catalyst-derived impurities (−950 mg). 1H NMR (400 MHz, CHLOROFORM-d6) δ ppm 7.34 (d, J=8.0 Hz, 1H), 6.06 (d, J=8.1 Hz, 1H), 5.19 (m, 1H), 5.09 (m, 1H), 4.29 (br. s, 2H), 3.91 (s, 3H), 2.10 (s, 3H).

Workup

  1. customThe mixture was sealed in a microwave vial
  2. temperatureUpon cooling
  3. washwashed with water and brine
  4. concentrationconcentrated on to silica gel
  5. customchromatographed (10% to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-cc84789dfea94b2c847ce3c9f064c029
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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