Water → HCID 66591283, compound

HRID 1092276

Reaction equation

HRID 1092276 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.CN[C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.O.[CH3:21][N:22](C)C=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]2[CH:14]=[C:13]([CH2:21][NH2:22])[CH:12]=[CH:11][CH:16]=2)=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 693532,5-DibromopyridineHCID 23558980[3-(Methylamino)phenyl]boronic acid

Product 1

HCID 66591283HCID 66591283, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

2.2 g (9.5 mmol, 1.2 eq) of 2,5-dibromopyridine are dissolved in 3 mL of an 8/2 mixture of dimethylformamide/2M potassium phosphate. 1.2 g (7.9 mmol, 1 eq) of N-methyl-3-aminophenylboronic acid are added along with 456 mg (0.39 mmol, 5 mol %) of tetrakis(triphenylphosphine)palladium. The mixture is stirred for 3 hours at 90° C. The reaction is stopped by adding 30 mL of water and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated and the residue is then chromatographed on silica gel (80/20 to 70/30 heptane/ethyl acetate). 1.07 g of [3-(5-bromopyrid-2-yl)phenyl]methylamine are obtained. Yield 52%.

Workup

  1. extractionis then extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated
  4. customthe residue is then chromatographed on silica gel (80/20 to 70/30 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-5462fe44302a4c3a93cb4fa2f07ab868
Source dataset
uspto-grants-2012_03
Patent number
US08129416B2

Linked notes

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