Boron tribromide → HCID 178515923, compound

HRID 57291Notes

Reaction equation

HRID 57291 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([C:14]3[S:15][C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=4[N:18]=3)=[CH:12][NH:11][N:10]=2)=[CH:5][CH:4]=1.BrB(Br)Br>C(Cl)Cl>[S:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=[C:14]1[C:13]1[C:9]([C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)=[N:10][NH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178489153HCID 178489153, compound

Product 1

HCID 178515923HCID 178515923, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-[3-(4-methoxyphenyl)-1H-pyrazol-4-yl]benzothiazole (100 mg, 0.33 mmol) was slowly added tribromoborane (3.3 mL of a 1 M solution in CH2Cl2, 3.3 mmol). The mixture was stirred overnight. The reaction was then quenched by the addition of methanol. The mixture was neutralized with sodium carbonate solution and extracted three times with ethyl acetate. The organic extracts were combined, washed with brine, dried over Na2SO4, filtered, and evaporated. The crude material was recrystallized from ethyl acetate to yield 64 mg (66%) of the title compound as a yellow solid. MS (m/z, ES+): 294 (M+1, 100%). 1H NMR (400 MHz, ppm, DMSO-d6): δ 13.5 (br s, 1H), 9.80 (br s, 1H), 8.22 (br s, 1H), 7.98 (d, 3J=8.1 Hz, 1H), 7.91 (d, 3J=8.0 Hz, 1H), 7.47 (d, 3J=8.0 Hz, 2H), 7.45 (dd, 3J=7.4 Hz, 3J=8.1 Hz, 1H), 7.34 (dd, 3J=7.4 Hz, 3J=8.0 Hz, 1H), 6.89 (d, 3J=8.0 Hz, 2H).

Workup

  1. customThe reaction was then quenched by the addition of methanol
  2. extractionextracted three times with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude material was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5401649e3a044d778bb5da2978718de8
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Reaction notes

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