Thiourea → HCID 59825041, compound

HRID 886634Notes

Reaction equation

HRID 886634 reaction equation
Br[CH2:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([Br:14])[CH:12]=2)[NH:7][CH:6]=1)=O.[NH2:15][C:16]([NH2:18])=[S:17]>C(O)C>[Br:14][C:11]1[CH:12]=[C:13]2[C:5]([C:3]3[S:17][C:16]([NH2:18])=[N:15][CH:2]=3)=[CH:6][NH:7][C:8]2=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 597000532-Bromo-1-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one

Product 1

HCID 59825041HCID 59825041, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromo-1-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanone (0.5 g, 1.6 mmol), thiourea (180 mg, 2.4 mmol) in ethanol (15 ml) were stirred at 100° C. under nitrogen overnight. Solvent was removed and the crude was titurated with DCM, filtered, and washed with more DCM afforded 5-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-ylamine (114 mg, 24% yield). 1H NMR (500 MHz, DMSO-d6) δ 7.21 (s, 1H), 8.15 (s, 1H), 8.42 (s, 1H), 8.58 (s, 1H), 8.98 (s, 2H), 12.42 (s, 1H). MS: m/z 295.0 (M+H+).

Workup

  1. customSolvent was removed
  2. filtrationfiltered
  3. washwashed with more DCM

Sources & evidence

ORD record
ord-d2336dc6f8d249659ca523d833e689a4
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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