Triacetoxyperiodinane → HCID 86642952, compound

HRID 1811121Notes

Reaction equation

HRID 1811121 reaction equation
[F:1][C:2]1[CH:35]=[CH:34][C:5]([C:6]([NH:8][C:9]2[C:10]([CH3:33])=[C:11]([C:15]3[C:27]4[C:26]5[C:21](=[CH:22][C:23]([CH2:28][OH:29])=[CH:24][CH:25]=5)[NH:20][C:19]=4[C:18]([C:30]([NH2:32])=[O:31])=[CH:17][CH:16]=3)[CH:12]=[CH:13][CH:14]=2)=[O:7])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[C:10]([CH3:33])=[C:11]([C:15]3[C:27]4[C:26]5[C:21](=[CH:22][C:23]([CH:28]=[O:29])=[CH:24][CH:25]=5)[NH:20][C:19]=4[C:18]([C:30]([NH2:32])=[O:31])=[CH:17][CH:16]=3)[CH:12]=[CH:13][CH:14]=2)=[O:7])=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59375141HCID 59375141, compound

Product 1

HCID 86642952HCID 86642952, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step 1 A solution of 4-(3-(4-fluorobenzamido)-2-methylphenyl)-7-(hydroxymethyl)-9H-carbazole-1-carboxamide (Example 31-4, 0.54 g, 1.155 mmol) in THF (38.5 mL) was treated with 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1 H)-one (Dess-Martin periodinane, 0.784 g, 1.848 mmol) at rt and the mixture was stirred for 2 h. The mixture was partitioned between NaHCO3 (aq) and EtOAc. The organic phase was washed with brine, dried and concentrated. The residue was triturated with methanol and the solid was collected by filtration and dried to provide 4-(3-(4-fluorobenzamido)-2-methylphenyl)-7-formyl-9H-carbazole-1-carboxamide as an orange solid (458 mg, 85%). 1H NMR (400 MHz, DMSO-d6) δ 11.98 (1 H, s), 10.16 (1 H, s), 10.03 (1 H, s), 8.23-8.32 (2 H, m), 8.05-8.14 (3 H, m), 7.60 (1 H, br. s.), 7.49-7.55 (1 H, m), 7.39-7.49 (2 H, m), 7.32-7.39 (2 H, m), 7.21-7.27 (1 H, m), 7.09 (2 H, t, J=8.1 Hz), 1.88 (3 H, s). Mass spectrum m/z 466.3 (M+H)+.

Workup

  1. customThe mixture was partitioned between NaHCO3 (aq) and EtOAc
  2. washThe organic phase was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was triturated with methanol
  6. filtrationthe solid was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-f3c2db90cfd840758df9a9ed0782df17
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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