Trimethyl borate → 2-Propynyl-6-fluoropyridin-5-ylboric acid

HRID 274188Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[N:5]=1)#[C:2][CH3:3].[Li+].CC([N-]C(C)C)C.[B:19]([O:24]C)([O:22]C)[O:20]C>>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([O:20][B:19]([OH:24])[OH:22])=[C:6]([F:10])[N:5]=1)#[C:2][CH3:3]

Participants

Reactant 3

HCID 8470Trimethyl borate

HCID 2724682Lithium diisopropylamide

HCID 450792522-Propyn-1-yl-6-fluoropyridine

Product 1

HCID 677830322-Propynyl-6-fluoropyridin-5-ylboric acid

Procedure

0.05 mol of 10A, 0.08 mol of LDA and 0.08 mol of trimethyl borate are reacted with one another analogously to Example 1B. Aqueous work-up gives the unpurified product, which is processed further as in 10C.

Sources & evidence

ORD record: ord-a3739a3bb60d49919ae412b401376986
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05389291

Reaction notes

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