Triphenylphosphine → 5-bromo-6-fluoro-3-(1-BOC-2-(S)-pyrrolidinylmethoxy)pyridine

HRID 365860Notes

Reaction equation

HRID 365860 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][OH:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:15][C:16]1[C:17]([F:23])=[N:18][CH:19]=[C:20](O)[CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:15][C:16]1[CH:21]=[C:20]([O:14][CH2:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][N:8]2[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH:19]=[N:18][C:17]=1[F:23]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 643448(S)-(-)-N-Boc-prolinolHCID 5462977Diethyl azodicarboxylateHCID 184587775-Bromo-6-fluoropyridin-3-ol

Product 1

HCID 228726705-bromo-6-fluoro-3-(1-BOC-2-(S)-pyrrolidinylmethoxy)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A sample of 1-BOC-2-(S)-pyrrolidinemethanol, prepared as described above, and of 3-bromo-2-fluoro-5-hydroxypyridine, prepared as in step b above, are reacted with triphenylphosphine and DEAD in THF at room temperature for 16 hours, to give the title compound.

Sources & evidence

ORD record
ord-49eab972cca149c38e8814a8ae066c1d
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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