Boron tribromide → HCID 57725507, compound

HRID 1922266Notes

Reaction equation

HRID 1922266 reaction equation
[Br:1][C:2]1[C:10]2[S:9][C:8]([NH:11][C@@H:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]3[OH:18])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:19]C.B(Br)(Br)Br>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[C:10]2[S:9][C:8]([NH:11][C@@H:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]3[OH:18])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:19]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 57725478HCID 57725478, compound

Product 1

HCID 57725507HCID 57725507, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To the solution of (1R,2R)-2-(7-bromo-6-methoxybenzo[d]thiazol-2-ylamino) cyclohexanol (191 mg, 0.537 mmol, 1.0 eq) in 10 mL of DCM was added 1 M solution of boron tribromide (ca. 3.0 mL, 2.68 mmol, 5.0 eq) at room temperature. The reaction mixture was refluxed for 12 hours, thereafter the mixture was diluted with saturated sodium bicarbonate (ca. 100 mL) till PH=7 and aqueous layer extracted with ethyl acetate (ca. 150 mL×3). Combined organic layers were dried over sodium sulfate, filtered and condensed under reduced pressure to give sufficiently pure crude product which was carried to next step without further purification LC/MS (m/z) [345.0] (MH+).

Workup

  1. temperatureThe reaction mixture was refluxed for 12 hours
  2. extractionextracted with ethyl acetate (ca. 150 mL×3)
  3. dry with materialCombined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customcondensed under reduced pressure
  6. customto give sufficiently pure crude product which
  7. customwas carried to next step without further purification LC/MS (m/z) [345.0] (MH+)

Sources & evidence

ORD record
ord-221815f8cb094649b8bb331c477cff3a
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

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