Triisopropyl borate → HCID 58415280, compound

HRID 2075208Notes

Reaction equation

HRID 2075208 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]3[S:12][CH:13]=[CH:14][N:15]=3)=[CH:9][C:4]=2[CH:3]=[CH:2]1.[Li]CCCC.[B:21](OC(C)C)([O:26]C(C)C)[O:22]C(C)C>C1COCC1>[S:12]1[CH:13]=[CH:14][N:15]=[C:11]1[CH2:10][C:8]1[CH:7]=[CH:6][C:5]2[O:1][C:2]([B:21]([OH:26])[OH:22])=[CH:3][C:4]=2[CH:9]=1

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 58415294HCID 58415294, compoundHCID 178418339Butyllithium

Product 1

HCID 58415280HCID 58415280, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-(benzofuran-5-ylmethyl)thiazole (0.68 g, 3 mmol) in THF (20 mL) was cooled to −78° C. (under argon), treated with 2.5 M n-BuLi (3.0 equiv, 3.6 mL, in hexanes), and stirred for 2 min, warmed to 0° C. for 30 min, cooled to −78° C., and treated with triisopropyl borate (1 mL, 6 mmol). After 5 min, cooling was removed and the mixture slowly warmed to room temperature and stirred for 2 h. The mixture was diluted with EtOAc, washed 1× with brine, dried over MgSO4 and evaporated to give 5-(thiazol-2-ylmethyl)benzofuran-2-ylboronic acid as a yellow solid. MS (ESI) m/z: Calculated: 259.1; Observed: 260.4 (M++1).

Workup

  1. temperaturecooled to −78° C.
  2. waitAfter 5 min
  3. temperaturecooling
  4. customwas removed
  5. temperaturethe mixture slowly warmed to room temperature
  6. stirringstirred for 2 h
  7. additionThe mixture was diluted with EtOAc
  8. washwashed 1× with brine
  9. dry with materialdried over MgSO4
  10. customevaporated

Sources & evidence

ORD record
ord-ef85203973c041f08aee57870b6f6de6
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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