Potassium Carbonate → [(2-Bromo-4-{[(3,4-dichloro-phenyl)-(4-phenyl-thiazol-2-yl)-amino]-methyl}-phenyl)-difluoro-methyl]-phosphonic acid diethyl ester

HRID 130351Notes

Reaction equation

HRID 130351 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C([O-])([O-])=O.[K+].[K+].[CH2:27]([O:29][P:30]([C:35]([C:38]1[CH:43]=[CH:42][C:41]([CH2:44]Br)=[CH:40][C:39]=1[Br:46])([F:37])[F:36])(=[O:34])[O:31][CH2:32][CH3:33])[CH3:28]>CN(C=O)C>[CH2:32]([O:31][P:30]([C:35]([C:38]1[CH:43]=[CH:42][C:41]([CH2:44][N:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[CH:40][C:39]=1[Br:46])([F:37])[F:36])(=[O:34])[O:29][CH2:27][CH3:28])[CH3:33]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18374434Diethyl (2-bromo-4-(bromomethyl)phenyl)(difluoro)methylphosphonateHCID 86228547(3,4-Dichloro-phenyl)-(4-phenyl-thiazol-2-yl)-amine

Product 1

HCID 86607370[(2-Bromo-4-{[(3,4-dichloro-phenyl)-(4-phenyl-thiazol-2-yl)-amino]-methyl}-phenyl)-difluoro-methyl]-phosphonic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (3,4-Dichloro-phenyl)-(4-phenyl-thiazol-2-yl)-amine (0.34 g, 1.04 mmol) in DMF (5 mL) was added K2CO3 (0.23 g, 1.71 mmol). After 0.1 hour, [(2-Bromo-4-bromomethyl-phenyl)-difluoro-methyl]-phosphonic acid diethyl ester (0.15 g, 0.34 mmol) was added and the resulting mixture was stirred at room temperature overnight. The reaction was partitioned between ethyl acetate and H2O, after which the organic layer was dried over NaSO4 and concentrated in vacuo. The resulting material was purified via column chromatography (1/1 hexanes/ethyl acetate) to yield 0.176 g (76%) of a clear, colorless oil; 1H NMR (300 MHz, CDCl3) δ 7.84-7.22 (m, 11 H), 6.81 (s, 1 H), 5.23 (s, 2 H), 4.23 (m, 4 H), 1.31 (t, J=7.5 Hz, 6 H).

Workup

  1. customThe reaction was partitioned between ethyl acetate and H2O
  2. dry with materialafter which the organic layer was dried over NaSO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting material was purified via column chromatography (1/1 hexanes/ethyl acetate)
  5. customto yield 0.176 g (76%) of a clear, colorless oil

Sources & evidence

ORD record
ord-6131da2cc40b47ba9cf8522034cf0c25
Source dataset
uspto-grants-2008_06
Patent number
US07381736B2

Reaction notes

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