Triacetoxyperiodinane → HCID 86642953, compound

HRID 1811123Notes

Reaction equation

HRID 1811123 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:19]3[C:14](=[CH:15][C:16]([CH2:21][OH:22])=[CH:17][CH:18]=3)[NH:13][C:12]=2[C:11]([C:23]([NH2:25])=[O:24])=[CH:10][CH:9]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl.C(#N)C.C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:19]3[C:14](=[CH:15][C:16]([CH:21]=[O:22])=[CH:17][CH:18]=3)[NH:13][C:12]=2[C:11]([C:23]([NH2:25])=[O:24])=[CH:10][CH:9]=1

Participants

7

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59375101HCID 59375101, compound

Product 1

HCID 86642953HCID 86642953, compound

Reagents, catalysts & solvents 4

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Step 1 A solution of 4-(2-fluorophenyl)-7-(hydroxymethyl)-9H-carbazole-1-carboxamide (Example 30-1, 147 mg, 0.440 mmol) in DCM (3 mL), acetonitrile (5 mL) and THF (3 mL) was treated with 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1 H)-one (Dess-Martin periodinane, 373 mg, 0.879 mmol). After 30 min at rt, the mixture was diluted with EtOAc (30 mL), washed twice with 1 M aqueous sodium sulfite and brine, dried and concentrated to give 4-(2-fluorophenyl)-7-formyl-9H-carbazole-1-carboxamide as a tan solid (ca. 80% purity, 163 mg, 87%), used without purification. Mass spectrum m/z 333.1 (M+H)+.

Workup

  1. washwashed twice with 1 M aqueous sodium sulfite and brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e9d4691f3cdc44a6bc72355e2b23865a
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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