Sodium Iodide → HCID 66701114, compound

HRID 2075521Notes

Reaction equation

HRID 2075521 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:10][C:11]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[OH:23])=[O:12])[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].Cl[CH2:33][C:34]1[CH:35]=[CH:36][C:37]([C:40]([F:43])([F:42])[F:41])=[N:38][CH:39]=1>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1([NH:10][C:11]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[O:23][CH2:33][C:34]2[CH:39]=[N:38][C:37]([C:40]([F:43])([F:41])[F:42])=[CH:36][CH:35]=2)=[O:12])[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 27738105-(Chloromethyl)-2-(trifluoromethyl)pyridineHCID 59707047HCID 59707047, compound

Product 1

HCID 66701114HCID 66701114, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.3 mmol 1-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-cyclobutanecarboxylic acid ethyl ester (94 mg), 0.6 mmol cesium carbonate (196 mg) (0.75 mmol in case of non-benzylic halides, +1 eq. in case of hydrochlorides) and 0.03 mmol sodium iodide (4 mg) are stirred for 10 min in 3 ml dry DMF. 0.33 mmol 5-Chloromethyl-2-trifluoromethyl-pyridine (65 mg) (0.45 mmol in case of non-benzylic halides) is added and the mixture is stirred for 2 h at RT and then for 5 h at 80° C. The cooled mixture is filtered, the filter washed with 5 ml ethyl acetate, the filtrate diluted with 20 ml ethyl acetate and washed twice with 20 ml 5% brine. The organic phase is dried and evaporated to yield 140 mg of 1-{[1-(6-Tri-fluoromethyl-pyridin-3-ylmethoxy)-naphthalene-2-carbonyl]-amino}-cyclobutane-carboxylic acid ethyl ester.

Workup

  1. waitfor 5 h at 80° C
  2. filtrationThe cooled mixture is filtered
  3. washthe filter washed with 5 ml ethyl acetate
  4. additionthe filtrate diluted with 20 ml ethyl acetate
  5. washwashed twice with 20 ml 5% brine
  6. customThe organic phase is dried
  7. customevaporated

Sources & evidence

ORD record
ord-a78762c335cc48dd8c8f985ed182cd15
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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