Boron tribromide → HCID 59374178, compound

HRID 473672Notes

Reaction equation

HRID 473672 reaction equation
[F:1][C:2]1[C:3]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[C:3]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 59374207HCID 59374207, compound

Product 1

HCID 59374178HCID 59374178, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

The solution of 3-fluoro-N-(4-methoxyphenyl)pyridin-2-amine (0.50 g, 0.002 mol) in DCM (20 mL) was cooled to −40° C. and to it was added boron tribromide (1.14 g, 0.0045 mol) dropwise under nitrogen over 30 mins. The reaction mixture was stirred at −40° C. for 1 h then at RT for another 2 h. The reaction mixture was cooled at 0° C. and saturated sodium bicarbonate was added. After stirring for 30 mins, the reaction was extracted with ethyl acetate (20×3 mL). Combined organic extracts were dried over sodium sulfate and concentrated to give the desired product which was used directly in the next step. MS (ESI, pos. ion) m/z: 205.19 (M+1).

Workup

  1. waitat RT for another 2 h
  2. temperatureThe reaction mixture was cooled at 0° C.
  3. stirringAfter stirring for 30 mins
  4. extractionthe reaction was extracted with ethyl acetate (20×3 mL)
  5. dry with materialCombined organic extracts were dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c04d1e03be84436aabcf2886aef26359
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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