Boron tribromide → HCID 136350295, compound

HRID 1506419Notes

Reaction equation

HRID 1506419 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[C:12]1[S:11][C:10]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:17]=3[C:27]([F:30])([F:29])[F:28])=[N:9][C:8]=1[CH2:7][CH2:6]2.B(Br)(Br)Br>ClCCl>[C:21]1([C:18]2[C:17]([C:27]([F:30])([F:29])[F:28])=[C:16]([C:10]3[S:11][C:12]4[C:13]5[C:5](=[CH:4][C:3]([OH:2])=[CH:15][CH:14]=5)[CH2:6][CH2:7][C:8]=4[N:9]=3)[O:20][N:19]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67171557HCID 67171557, compound

Product 1

HCID 136350295HCID 136350295, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(7-methoxy-4,5-dihydronaphtho[2,1-d]thiazol-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole (Preparation 56B, 0.448 g, 1.046 mmol) in dichloromethane (13.07 mL) was added 1M BBr3 (5.23 mL, 5.23 mmol) in dichloromethane dropwise, and the mixture was stirred at room temperature for 4.5 h. The reaction was slowly quenched with sat. NaHCO3. After stirring for 5 min, sat. NH4Cl was added. It was then partitioned between dichloromethane and water. The aqueous layer was extracted with dichloromethane. The combined organic layers were then washed with brine, dried over anhydrous MgSO4, concentrated and chromatographed to give the 2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]thiazol-7-ol (0.388 g, 0.936 mmol, 90% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.63-7.69 (2H, m), 7.46-7.58 (3H, m), 7.31 (1H, d, J=8.14 Hz), 6.80 (1H, d, J=2.42 Hz), 6.76 (1H, dd, J=8.25, 2.53 Hz), 3.15-3.23 (2H, m), 3.05-3.14 (2H, m).

Workup

  1. customThe reaction was slowly quenched with sat. NaHCO3
  2. stirringAfter stirring for 5 min
  3. additionsat. NH4Cl was added
  4. customIt was then partitioned between dichloromethane and water
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. washThe combined organic layers were then washed with brine
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated
  9. customchromatographed

Sources & evidence

ORD record
ord-15ff5ab1e304405bb63575e66fd002d2
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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