Triisopropyl borate → HCID 59887844, compound

HRID 551274Notes

Reaction equation

HRID 551274 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[Cl:12])=[CH:4][CH:3]=1.[B:13](OC(C)C)([O:18]C(C)C)[O:14]C(C)C.C([Li])CCC>C1COCC1>[Cl:12][C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([B:13]([OH:18])[OH:14])[CH:11]=2)[CH:6]=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 65020247-Bromo-1-ChloroisoquinolineHCID 178418339Butyllithium

Product 1

HCID 59887844HCID 59887844, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

7-Bromo-1-chloroisoquinoline (1.38 g, 5.69 mmol) in THF (15 mL) under nitrogen, at −78° C. and triisopropyl borate (2.99 g, 15.93 mmol) added, followed by dropwise addition of n-butyllithium (7.11 mL of 1.6M in hexanes, 11.38 mmol). Allowed reaction mixture to warm to −20° C. over 30 minutes and quenched with 1N HCl (30 mL). Added triethylamine to give pH 7, presorbed solution directly onto silica and flash column chromatography on silica gel to give the product as pale yellow solid (0.78 g, 3.8 mmol). 1H NMR (DMSO) δ 8.73 (s, 1H), 8.48 (br s, 2H), 8.35-8.28 (m, 1H), 8.25-8.13 (m, 1H), 8.06-7.92 (m, 1H), 7.91-7.82 (m, 1H). ESI MS (M+1)+: 208, 210 (Cl).

Workup

  1. customAllowed reaction mixture
  2. customquenched with 1N HCl (30 mL)
  3. customAdded triethylamine to give pH 7

Sources & evidence

ORD record
ord-c44ce3d9b10a428fb97dc3c9446e45ee
Source dataset
uspto-grants-2011_05
Patent number
US07947684B2

Reaction notes

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