Trimethyl borate → HCID 86715118, compound

HRID 533932Notes

Reaction equation

HRID 533932 reaction equation
[Br:1][C:2]1[C:3]([O:9][CH2:10][CH:11]2[CH2:13][CH2:12]2)=[N:4][CH:5]=[C:6](I)[CH:7]=1.C([Mg]Cl)(C)C.B(OC)(OC)[O:20]C>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([OH:20])[CH:5]=[N:4][C:3]=1[O:9][CH2:10][CH:11]1[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 86715119HCID 86715119, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 86715118HCID 86715118, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-bromo-2-(cyclopropylmethoxy)-5-iodopyridine (12.5 g) in dry THF (300 mL) was added i-PrMgCl*LiCl (30 mL, 38.3 mmol) dropwise at 0° C. The mixture was stirred at 0° C. for 20 min and then B(OMe)3 (5.5 g) was added at 0° C. The mixture was allowed to warm to r.t. and stirred for 3 h. The mixture was quenched by the addition of brine (50 mL). The organic phase was separated and the aqueous phase was extracted with EA (50 mL×3). The organic phases were combined and the solvent was removed under reduced pressure. The residue was treated according Typical Procedure 5a to obtain the title compound. MS ESI+: m/z=244 [M+H]+.

Workup

  1. temperatureto warm to r.t.
  2. stirringstirred for 3 h
  3. customThe mixture was quenched by the addition of brine (50 mL)
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with EA (50 mL×3)
  6. customthe solvent was removed under reduced pressure
  7. additionThe residue was treated

Sources & evidence

ORD record
ord-d46fac5c8e0346b5bffb0debbb423c9d
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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