1,1'-Carbonyldiimidazole → HCID 69236140, compound

HRID 1593652Notes

Reaction equation

HRID 1593652 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:5]=[C:6]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]1[CH2:11][CH2:10][CH:9]([C:17](O)=[O:18])[CH2:8][C:7]2=1.C(N1C=CN=C1)([N:24]1C=CN=C1)=O>O1CCCC1>[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:5]=[C:6]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]1[CH2:11][CH2:10][CH:9]([C:17]([NH2:24])=[O:18])[CH2:8][C:7]2=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 21548611HCID 21548611, compound

Product 1

HCID 69236140HCID 69236140, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 6-(trifluoromethoxy)-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid of Step 2 (1.722 g, 5.75 mmol) in anhydrous tetrahydrofuran (37 mL) was treated under nitrogen with carbonyldiimidazole (1.37 g, 8.61 mmol). The yellow solution was stirred at room temperature for 5 hours and then anhydrous ammonia was bubbled through the solution for 30 minutes. The suspension was diluted with ethyl acetate and the organic phase was washed with 1:1 water/saturated aqueous sodium bicarbonate and 1:1 water/brine. The extracts were dried over anhydrous magnesium sulfate and evaporated to dryness to yield a pale yellow glass. The residue was purified by chromatography on silica gel Merck-60 using a 1% to 3% gradient of methanol in dichloromethane to provide the title compound (1.33 g, 77%) as an off white solid, m.p. 177-178° C. MS [(+)ES, m/z]: 299 [M+H]+. HRMS [(+)ESI, m/z]: 299.1004 [M+H]+. Calc'd for C14H14F3N2O2: 299.1007. HPLC: Chromolith Monolith column, 0.46×10 cm, gradient of acetonitrile in water (0.01% TFA), 4 mL/min, detection at 254 nm; Rt 1.8 min.

Workup

  1. customanhydrous ammonia was bubbled through the solution for 30 minutes
  2. additionThe suspension was diluted with ethyl acetate
  3. washthe organic phase was washed with 1:1 water/saturated aqueous sodium bicarbonate and 1:1 water/brine
  4. dry with materialThe extracts were dried over anhydrous magnesium sulfate
  5. customevaporated to dryness
  6. customto yield a pale yellow glass
  7. customThe residue was purified by chromatography on silica gel Merck-60

Sources & evidence

ORD record
ord-d4c349353c0e470786efafe9b11c2246
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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