Triacetoxyperiodinane → 4-(4-Dimethylcarbamoyl-3-fluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (5-formyl-pyridin-2-yl)-amide

HRID 1177128Notes

Reaction equation

[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([C:12]2[CH:22]=[C:21]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30](=[O:34])[N:31]([CH3:33])[CH3:32])=[C:26]([F:35])[CH:25]=3)[C:15]3[CH2:16][C:17]([CH3:20])([CH3:19])[O:18][C:14]=3[CH:13]=2)=[O:11])=[N:7][CH:8]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([C:12]2[CH:22]=[C:21]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30](=[O:34])[N:31]([CH3:33])[CH3:32])=[C:26]([F:35])[CH:25]=3)[C:15]3[CH2:16][C:17]([CH3:20])([CH3:19])[O:18][C:14]=3[CH:13]=2)=[O:11])=[N:7][CH:8]=1)=[O:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-(4-Dimethylcarbamoyl-3-fluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (5-hydroxymethyl-pyridin-2-yl)-amide (145) (88 mg, 0.18 mmol) in 3 mL CH2Cl2 was added Dess-Martin periodinane (93.4 mg, 0.22 mmol) at 0° C. The mixture was stirred at 0° C. for 1.5 hr. The reaction was quenched with water, extracted with 3×CHCl3. The combined organic layer was dried with Na2SO4 and concentrated. The resulting oil was taken into the next step without further purification. LCMS for C26H24FN3O5 m/z 478.20 (M+H+).

Workup

customThe reaction was quenched with water
extractionextracted with 3×CHCl3
dry with materialThe combined organic layer was dried with Na2SO4
concentrationconcentrated
customThe resulting oil was taken into the next step without further purification

Sources & evidence

ORD record: ord-8bba4ffec5a042a29fb899b6ad957637
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842713B2

Reaction notes

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