9-Borabicyclo(3.3.1)nonane → HCID 57722791, compound

HRID 1987127Notes

Reaction equation

HRID 1987127 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[CH:14]=[C:15]([CH:18]=[CH2:19])[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.B1C2CCCC1CCC2>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:12]([OH:13])[C:11]3[CH:14]=[C:15]([CH2:18][CH3:19])[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 789669-Borabicyclo(3.3.1)nonaneHCID 57722897HCID 57722897, compound

Product 1

HCID 57722791HCID 57722791, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-chloro-7-vinyl-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (20 mg, 0.075 mmol) was dissolved in 1 mL of tetrahydrofuran. Rh(COD)2BF4 (3 mg, 0.007 mmol) was added followed by a dropwise addition of 9-BBN (0.44 mL of 0.5 M in THF, 0.22 mmol) and the reaction was stirred overnight. The reaction was cooled to 0° C. and quenched by the simultaneous addition of 1M sodium hydroxide (2.5 ml) and 30% aqueous hydrogen peroxide (0.75 mL) and stirred for 5 hours. The resulting solution was poured into ethyl acetate and brine and extracted three times with ethyl acetate. The combined organics were dried over magnesium sulfate, dried over magnesium sulfate, concentrated in vacuo, and purified via flash chromatography (0-60% ethyl acetate/hexanes) to afford the title compound. 1H NMR (600 MHz, CDCl3) δ 8.41 (s, 1H); 8.03 (s, 1H); 7.54 (s, 1H); 7.28 (m, 2H); 7.17-7.14 (m, 2H); 5.31 (s, 1H); 2.70 (q, 2H); 1.25 (t, 3H). Hydroxyl proton was not observed. LRMS (APCI) calc'd for (C16H15ClNO) [M+H]+, 272.1; found 272.1.

Workup

  1. customquenched by the simultaneous addition of 1M sodium hydroxide (2.5 ml) and 30% aqueous hydrogen peroxide (0.75 mL)
  2. stirringstirred for 5 hours
  3. additionThe resulting solution was poured into ethyl acetate and brine
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. custompurified via flash chromatography (0-60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d79d53d8e5cc41c3acb30cc71b5a76a1
Source dataset
uspto-grants-2009_06
Patent number
US07550478B2

Reaction notes

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