Boron tribromide → 1054629-49-0

HRID 501059Notes

Reaction equation

HRID 501059 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][C:18]=3[CH:19]=2)=[C:11]([F:26])[N:10]=1)C)(C)(C)C.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[F:26][C:11]1[C:12]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][C:18]=3[CH:19]=2)=[CH:13][CH:14]=[C:9]([NH:7][CH3:6])[N:10]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 25015017HCID 25015017, compound

Product 1

HCID 248966051054629-49-0Yield 41.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [6-fluoro-5-(5-methoxy-benzofuran-2-yl)-pyridin-2-yl]-methyl-carbamic acid tert-butyl ester (66 mg, 0.184 mmol) in dichloromethane (30 mL) at 0° C. under nitrogen atmosphere, BBr3 (1M solution in CH2Cl2, 0.92 mL, 0.92 mmol) was added dropwise. The reaction mixture was stirred at room temperature overnight and then cooled to 0° C. Saturated sodium bicarbonate solution was added and the resulting mixture was extracted subsequently with 5% methanol in dichloromethane and with 5% methanol in ethyl acetate. The organic layers were washed with brine separately, dried over Na2SO4, filtered, concentrated and flash chromatographed using 30% ethyl acetate in hexane to give) 2-(2-fluoro-6-methylamino-pyridin-3-yl)-benzofuran-5-ol (19.9 mg) as a off white solid. 1H NMR (400 MHz, METHANOL-d4) δ: 8.02 (m, 1H), 7.27 (d, J=8.59 Hz, 1H), 6.90 (d, J=2.34 Hz, 1H), 6.77 (d, J=3.51 Hz, 1H), 6.70 (dd, J=8.59, 2.34 Hz, 1H), 6.43 (dd, J=8.59, 1.95 Hz, 1H), 2.89 (s, 3H). ESMS: m/z 259.47 [M+1]+

Workup

  1. temperaturecooled to 0° C
  2. extractionthe resulting mixture was extracted subsequently with 5% methanol in dichloromethane and with 5% methanol in ethyl acetate
  3. washThe organic layers were washed with brine separately
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customflash chromatographed

Sources & evidence

ORD record
ord-8fd3706a17fa4278a9488c2365458feb
Source dataset
uspto-grants-2010_08
Patent number
US07772256B2

Reaction notes

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