Boron tribromide → HCID 178426230, compound

HRID 539557Notes

Reaction equation

HRID 539557 reaction equation
[C:1]1([CH3:26])[CH:6]=[CH:5][C:4]([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:3][CH:2]=1.B(Br)(Br)Br>C(Cl)Cl>[C:1]1([CH3:26])[CH:6]=[CH:5][C:4]([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:3][CH:2]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178490057HCID 178490057, compound

Product 1

HCID 178426230HCID 178426230, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Reaction of 165a (0.075 g, 0.203 mmol) and 1M BBr3 (0.24 mL) in CH2Cl2 (8 mL) within 48 h as described for the synthesis of 148a gave compound 167a (0.042 g, 62%) as olive green solid. 1H NMR (400 MHz, CD3OD) δ 8.18 (s, 1H), 7.66 (d, J=8.0 Hz, 2H), 7.55 (d, J=5.7 Hz, 1H), 7.20 (d, J=7.7 Hz, 2H), 6.97 (d, J=6.7 Hz, 1H), 4.55 (m, 2H), 4.43 (t, J=6.7 Hz, 2H), 2.34 (s, 3H), 2.01 (m, 4H), 1.39 (t, J=22.5 Hz, 2H). 13C NMR (100 MHz, CD3OD) δ 149.25, 139.68, 130.93, 129.13, 127.01, 122.27, 51.41, 30.95, 24.51, 21.83. HRMS (EI) calcd for C19H22N4OS [M]+ 354.151. found 354.1512.

Sources & evidence

ORD record
ord-5c97d7bcc672492f98fabd33df98aeae
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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