Boron tribromide → HCID 178425445, compound

HRID 539558Notes

Reaction equation

HRID 539558 reaction equation
[C:1]1([CH3:26])[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]3[N:19]=[N:20][NH:21][CH:22]=3)=[C:9]([O:23]C)[C:8]2=[S:25])[CH:2]=1.B(Br)(Br)Br>C(Cl)Cl>[C:1]1([CH3:26])[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]3[N:19]=[N:20][NH:21][CH:22]=3)=[C:9]([OH:23])[C:8]2=[S:25])[CH:2]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178490056HCID 178490056, compound

Product 1

HCID 178425445HCID 178425445, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Reaction of 165b (0.10 g, 0.271 mmol) and 1M BBr3 (0.33 mL) in CH2Cl2 (8 mL) within 48 h as described for the synthesis of 148a gave compound 167b (0.053 g, 56%) as olive green solid. 1H NMR (400 MHz, CD3OD) δ 8.20 (s, 1H), 7.61 (s, 1H), 7.55 (m, 2H), 7.26 (t, J=7.6 Hz, 1H), 7.12 (d, J=7.5 Hz, 1H), 6.92 (m, 2H), 4.55 (m, 2H), 4.44 (t, J=6.7 Hz, 2H), 2.36 (s, 3H), 2.01 (m, 4H), 1.41 (m, 2H). 13C NMR (100 MHz, CD3OD) δ 149.29, 140.05, 131.87, 131.78, 130.38, 130.20, 127.90, 127.63, 124.13, 122.51, 51.40, 31.07, 30.93, 28.97, 24.49, 22.02. HRMS (EI) calcd for C19H22N4OS [M]+ 354.151. found 354.1523.

Sources & evidence

ORD record
ord-a788f60bb0874784a357f752458ae117
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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