Thiourea → 4-(4-Fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-ylamine

HRID 2108736Notes

Reaction equation

HRID 2108736 reaction equation
Br[CH2:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[F:14])[NH:7][CH:6]=1)=O.[NH2:15][C:16]([NH2:18])=[S:17]>C(O)C>[F:14][C:12]1[CH:11]=[CH:10][N:9]=[C:8]2[NH:7][CH:6]=[C:5]([C:3]3[N:15]=[C:16]([NH2:18])[S:17][CH:2]=3)[C:13]=12

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 57421973Ethanone, 2-bromo-1-(4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-

Product 1

HCID 576331034-(4-Fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-ylamineYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To an ethanol suspension of 2-bromo-1-(4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanone (3.00 g 0.0117 mol) was added thiourea (1.18 g, 0.0234 mol), the reaction mixture was heated at 70° C. for 1 h. The suspension was filtered while still warm and to the filtration cake was added sat. sodium carbonate solution until the aqueous phase pH was around 7.5. The suspension was filtered to afford 1.8 g free base (75%). H NMR, DMSO-d6: 6.78 (s, 1H), 6.9 (s, br, 2H), 6.98 (m, 1H), 7.71 (s, 1H), 8.25 (m, 1H).

Workup

  1. filtrationThe suspension was filtered
  2. temperaturewhile still warm and to the filtration cake
  3. additionwas added sat. sodium carbonate solution until the aqueous phase pH was around 7.5
  4. filtrationThe suspension was filtered

Sources & evidence

ORD record
ord-3097e10220934020a7dc21d448e293ee
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

Loading…