Trifluoroacetic anhydride → 4-(3-{[1-(Diphenylmethyl)azetidin-3-yl]oxy}-2-hydroxypropoxy)-1H-indole-2-carbonitrile

HRID 2107533Notes

Reaction equation

HRID 2107533 reaction equation
[C:1]1([CH:7]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:8]2[CH2:11][CH:10]([O:12][CH2:13][CH:14]([OH:29])[CH2:15][O:16][C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[C:20]([C:26]([NH2:28])=O)[NH:21]4)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1.N1C=CC=CC=1>[C:30]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:11][CH:10]([O:12][CH2:13][CH:14]([OH:29])[CH2:15][O:16][C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[C:20]([C:26]#[N:28])[NH:21]4)[CH2:9]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 23046050HCID 23046050, compound

Product 1

HCID 1237654-(3-{[1-(Diphenylmethyl)azetidin-3-yl]oxy}-2-hydroxypropoxy)-1H-indole-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent2×

Procedure

10.0 g of 4-(3-(1-diphenylmethylazetidin-3-oxy)-2-hydroxypropoxy)-1H-indole-2-carboxamide are dissolved in a mixture of 112 ml of dioxane and 10 g of pyridine and 10 ml of trifluoroacetic anhydride in 10 ml of dioxane are added at 10° C. After standing for two hours at room temperature, the mixture is stirred into ice water. The mixture is extracted using methylene chloride, washed first with dilute NaOH, then with water, and the organic phase is dried over sodium sulphate and concentrated. The residue is purified by column chromatography on silica gel (eluent: chloroform).

Workup

  1. additionare added at 10° C
  2. extractionThe mixture is extracted
  3. washwashed first with dilute NaOH
  4. dry with materialwith water, and the organic phase is dried over sodium sulphate
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography on silica gel (eluent: chloroform)

Sources & evidence

ORD record
ord-47812dab59114af5a8abc1f82668b1e4
Source dataset
uspto-grants-1990_06
Patent number
US04935414

Reaction notes

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