Dimethylformamide → HCID 57425159, compound

HRID 655931Notes

Reaction equation

HRID 655931 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][N:6]=[CH:5]2.CN(C=O)C.[Br:19][C:20]1[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=1>CCOC(C)=O>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([N:6]2[CH:5]=[C:4]3[C:8]([C:9]([C:11]([NH2:13])=[O:12])=[CH:10][C:2]([F:1])=[CH:3]3)=[N:7]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 99931-Bromo-4-fluorobenzeneHCID 574251635-Fluoro-1H-indazole-7-carboxamide

Product 1

HCID 57425159HCID 57425159, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of D2 (1.0 eq) in DMF (0.2 M) K2CO3 (1.3 eq) and 4-bromofluorobenzene (10.0 eq) were added and the reaction mixture was heated under MW conditions at 180° C. for 20 min. The reaction mixture was cooled to RT and diluted with EtOAc. The organic phase was washed with brine; dried (Na2SO4). Evaporation of the solvent gave (D3) which was purified by chromatography on silica gel eluting with 50-70% EtOAc/Petroleum ether to obtain the title compound as a yellow powder. 1H NMR (400 MHz, DMSO-d6, 300K) δ 9.34 (1H, s), 8.50 (1H, br. s), 8.17 (2H, d, J=9.0 Hz), 8.03 (1H, br. s), 7.90-7.80 (4H, m). MS (ES+) C14H9BrFN3O requires: 334/336. Found: 335/337 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-c073adb2f40e41bbba19d77f22b97c3e
Source dataset
uspto-grants-2011_12
Patent number
US08071623B2

Reaction notes

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