Bromoacetyl bromide → HCID 57421976, compound

HRID 2108742Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[Al+3].[Cl-].[Cl-].[Cl-].Br[CH2:16][C:17](Br)=O.[NH2:20][C:21]([NH2:23])=[S:22]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:16]3[N:20]=[C:21]([NH2:23])[S:22][CH:17]=3)=[CH:6][NH:7][C:8]2=[N:9][CH:10]=1

Participants

Reactant 4

HCID 61147Bromoacetyl bromide

HCID 2723790Thiourea

HCID 6451240Aluminum(III) Chloride

HCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 57421976HCID 57421976, compound

Procedure

The title compound was synthesized in 2 steps in a manner similar to that described above using 5-chloro-7-azaindole (0.32 g, 1.17 mmol), AlCl3 (0.47 g, 3.51 mmol), bromoacetylbromide (0.1 mL, 1.46 mmol) and thiourea (0.158 g, 2.08 mmol) (0.21 g, 67.5%, 2 steps) as pale brown solid. Mass Spec.; MS 251 (M+1); 1H NMR(DMSO-d6, 500 MHz) δ 11.97(s, 1H), 8.50(d, 1H), 8.22(d,1H), 7.84(d,1H),7.02(brs,2H), 6.83(s,1H).

Sources & evidence

ORD record: ord-ae15787d11924702b4cbf22e4fa4f584
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514448B2

Reaction notes

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