4-Bromo-2-fluoroaniline → HCID 23589557, compound

HRID 1295756Notes

Reaction equation

HRID 1295756 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:24][CH3:25])=[C:8]2[N:13]([CH:14]=1)[N:12]=[CH:11][N:10]=[C:9]2NC1C=CC(C)=C(O)C=1)=[O:5])[CH3:2].[Br:26][C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[C:29]([F:34])[CH:28]=1>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:24][CH3:25])=[C:8]2[N:13]([CH:14]=1)[N:12]=[CH:11][N:10]=[C:9]2[NH:31][C:30]1[CH:32]=[CH:33][C:27]([Br:26])=[CH:28][C:29]=1[F:34])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 1230504-Bromo-2-fluoroanilineHCID 23589558HCID 23589558, compound2×

Product 1

HCID 23589557HCID 23589557, compound

Procedure

The title compound was prepared from Compound G of Example 96 (0.2 mmol) and 4-bromo-2-fluoro-aniline (76 mg, 0.3 mmol) by the procedure analogous with the preparation of Compound H of Example 96. Thus, when the reaction was complete it was concentrated and washed with 1 N aqueous HCl to provide a solid which was triturated with aqueous NaHCO3 and water and then dried to provide 58 mg (70.9%) white solid. MS: [M+H]+=409, 411 (1:1); 1H NMR (d-DMSO): δ 8.83 (s, 1H), 7.97-7.93 (m, 2H), 7.90 (s, 1H), 7.66 (d, J=8.4 Hz, 1H), 7.43 (d, J=8.4 Hz, 1H), 4.24 (q, J=7.5 Hz, 2H), 3.97 (s, 3H), 1.26 (t, J=7.0 Hz, 3H).

Workup

  1. concentrationwas concentrated
  2. washwashed with 1 N aqueous HCl
  3. customto provide a solid which
  4. customwas triturated with aqueous NaHCO3 and water
  5. customdried

Sources & evidence

ORD record
ord-2c4010db318d4dc59b7d32bd961b300c
Source dataset
uspto-grants-2007_07
Patent number
US07244733B2

Reaction notes

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