HCID 59402849, compound → HCID 59402938, compound

HRID 538510Notes

Reaction equation

HRID 538510 reaction equation
Br[C:2]1[S:6][C:5]([CH2:7][O:8][C:9]2[C:10]([F:19])=[C:11]([C:15]([F:18])=[CH:16][CH:17]=2)[C:12]([NH2:14])=[O:13])=[N:4][C:3]=1[C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[Br:28]>C(O)(=O)C.[Zn]>[Br:28][C:21]1[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:20]=1[C:3]1[N:4]=[C:5]([CH2:7][O:8][C:9]2[C:10]([F:19])=[C:11]([C:15]([F:18])=[CH:16][CH:17]=2)[C:12]([NH2:14])=[O:13])[S:6][CH:2]=1

Participants

4

Reactant 1

HCID 59402849HCID 59402849, compound

Product 1

HCID 59402938HCID 59402938, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 3-[5-Bromo-4-(2-bromo-5-methoxy-phenyl)-thiazol-2-ylmethoxy]-2,6-difluoro-benzamide (0.06 g, 0.0001 mol) in 6 ml of acetic acid was added zinc (0.06 g, 0.0001 mol). The reaction mixture was refluxed for 30 min. The reaction mixture was allowed to come at 25° C. The reaction mixture was filtered on celite bed; the product was precipitated by adding water to the filtrate. The white solid was filtered and dried (0.006 g, 12%). 1H NMR (DMSO, 400 MHz), 3.79 (s, 3H), 5.59 (s, 2H), 6.94 (dd, 1H, J=8.8 Hz (o-coupling), J=4.0 Hz), 7.09-7.15 (m, 1H), 7.27 (d, 1H, J-4.0 Hz), 7.40-7.43 (m, 1H), 7.63 (d, 1H, J=8.8 Hz (o-coupling), 7.89 (broad s, 1H), 8.11 (s, 1H), 8.18 (s, 1H); MS ES+ (455.08 & 457.08). HPLC (method 5) Rt=10.21 min.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 min
  2. customto come at 25° C
  3. filtrationThe reaction mixture was filtered on celite bed
  4. customthe product was precipitated
  5. additionby adding water to the filtrate
  6. filtrationThe white solid was filtered
  7. customdried (0.006 g, 12%)

Sources & evidence

ORD record
ord-415f4bb45fdc4de28d77ac30071c5f13
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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