Dichloromethane → HCID 178515886, compound

HRID 539551Notes

Reaction equation

HRID 539551 reaction equation
[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]3[N:16]=[N:17][NH:18][CH:19]=3)=[C:9]([O:20]C)[C:8]2=[S:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br.C(Cl)Cl>>[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]3[N:16]=[N:17][NH:18][CH:19]=3)=[C:9]([OH:20])[C:8]2=[S:22])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 178488795HCID 178488795, compound

Product 1

HCID 178515886HCID 178515886, compoundYield 93.1%

Procedure

Reaction of 160 (0.062 g, 0.198 mmol) and 1M BBr3 in CH2Cl2 (0.218 mmol) within 48 h as described for synthesis of 148a gave compound 161 (0.055 g, 93%) as a dark violet solid. 1H NMR (400 MHz, CDCl3) δ 8.40 (s, 1H), 7.73 (d, J=7.3 Hz, 2H), 7.51 (s, 1H), 7.40 (t, J=7.5 Hz, 2H), 7.33 (t, J=7.3 Hz, 1H), 6.95 (dd, J=9.2, 7.2 Hz, 2H), 6.46 (m, 1H), 5.08 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 168.47, 155.10, 147.75, 132.00, 129.82, 128.77, 128.30, 125.53, 120.90, 113.66, 112.61, 57.45, 46.41. HRMS (EI) calcd for C15H14N4OS [M]+ 298.088. found 298.0888.

Sources & evidence

ORD record
ord-233c4997edf44bc8b3cc2767a989e25a
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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