Phosphorus tribromide → HCID 22733829, compound

HRID 2084587Notes

Reaction equation

HRID 2084587 reaction equation
[P:1]([Br:4])(Br)[Br:2].[N:5]1([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1>N1C=CC=CC=1>[Br:2][P:1]([Br:4])[C:15]1[CH:14]=[N:13][CH:12]=[CH:11][C:10]=1[N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 755674-Pyrrolidinopyridine

Product 1

HCID 22733829HCID 22733829, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of PBr3 (8.8 g, 32.5 mm) in 100 mL of pyridine was treated with 4-pyrrolidinopyridine (5.0 g, 33.7 mm) over a period of 5 min. The resulting mixture was then stirred at room temperature for 3 days to give the crude 3-dibromophosphino-4-pyrrolidinopyridine (31P NMR: δ152.2 ppm). This compound was used directly for the next step without further purification. Next, polymer-supported secondary amines from Example 1 (9.0 g, 1.1 mmol/g, 9.9 mmol) was slowly added into the mixture above while stirring at room temperature for a period of 10 min. The resulting suspension was refluxed overnight before the solution was filtered off. The resin was washed with THF (2×50 mL), hexane (3×50 mL), CH2Cl2 (4×50 mL), and hexane (2×50 mL). The resulting resin was dried in vacuum overnight to yield the polymer-supported 3-P(Br)-4-(NC4H8)C5H3N. 31P NMR (202 MHz, CDCl3): δ168.4 ppm.

Sources & evidence

ORD record
ord-ca811e14beb74a42ba84046c07f75ab6
Source dataset
uspto-grants-2004_04
Patent number
US06716984B2

Reaction notes

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