Boron tribromide → 4-(4,5,6,7-Tetrahydrothiazolo[5,4-C]pyridin-2-YL)phenol

HRID 510467Notes

Reaction equation

HRID 510467 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][C:14]2[N:17]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=3)[S:19][C:13]=2[CH2:12]1)=O)C1C=CC=CC=1.B(Br)(Br)Br>C(O)C>[N:17]1[C:14]2[CH2:15][CH2:16][NH:11][CH2:12][C:13]=2[S:19][C:18]=1[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 666534232-(4-Methoxy-phenyl)-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid benzyl ester

Product 1

HCID 1357416634-(4,5,6,7-Tetrahydrothiazolo[5,4-C]pyridin-2-YL)phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-78 °C

Procedure

Compound 504 (18.0 g, 47.3 mmol) was dissolved in ethanol (300 ml). To the cooled (−78° C.) solution was added boron tribromide (5 eg, 236 mmol) dropwise. After one hour cooling was removed and the mixture was stirred 16 hrs at room temperature. The reaction was quenched with MeOH, the mixture was concentrated in vacuo to give compound 505 as an oil which was used in the next step without further purification.

Workup

  1. temperatureAfter one hour cooling
  2. customwas removed
  3. customThe reaction was quenched with MeOH
  4. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-fb40d5f174f14d7fab19d17b8835ff11
Source dataset
uspto-grants-2015_08
Patent number
US09096612B2

Reaction notes

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