Boron tribromide → HCID 178424308, compound

HRID 539559Notes

Reaction equation

HRID 539559 reaction equation
[C:1]1([CH3:26])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[N:19]=[N:20][NH:21][CH:22]=2)=[C:9]([O:23]C)[C:8]1=[S:25].B(Br)(Br)Br>C(Cl)Cl>[C:1]1([CH3:26])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[N:19]=[N:20][NH:21][CH:22]=2)=[C:9]([OH:23])[C:8]1=[S:25]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178490055HCID 178490055, compound

Product 1

HCID 178424308HCID 178424308, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Reaction of 165c (0.072 g, 0.195 mmol) and 1M BBr3 (0.30 mL) in CH2Cl2 (8 mL) within 48 h as described for the synthesis of 148a gave compound 167c (0.046 g, 67%) as olive green solid. 1H NMR (400 MHz, CD3OD) δ 7.94 (s, 1H), 7.61 (m, 1H), 7.47 (s, 1H), 7.21 (m, 1H), 6.97 (m, 1H), 6.76 (m, 1H), 4.52 (m, 1H), 4.45 (t, J=6.8 Hz, 1H), 2.38 (s, 1H), 2.01 (m, 2H), 1.43 (m, 1H). 13C NMR (100 MHz, CD3OD) δ 146.74, 135.53, 130.65, 129.46, 128.69, 128.21, 125.88, 122.79, 53.41, 49.83, 29.42, 27.32, 22.98, 20.55. HRMS (EI) calcd for C19H22N4OS [M]+ 354.151. found 354.1509.

Sources & evidence

ORD record
ord-4b2a3d2018cc4d00a15f5ca34a021e35
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

Loading…