Triacetoxyperiodinane → [3-benzyloxy-2-cyclopropylmethoxy-phenyl]-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

HRID 253452Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([O:27][CH2:28][CH:29]2[CH2:31][CH2:30]2)=[C:11]([CH:15]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[C:23]([Cl:26])[CH:24]=3)[NH:19][CH:18]=2)[OH:16])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O1CCCC1>[CH2:1]([O:8][C:9]1[C:10]([O:27][CH2:28][CH:29]2[CH2:30][CH2:31]2)=[C:11]([C:15]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[C:23]([Cl:26])[CH:24]=3)[NH:19][CH:18]=2)=[O:16])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of [3-benzyloxy-2-cyclopropylmethoxy-phenyl]-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (131, 0.99 g, 2.28 mmol) in tetrahydrofuran (120 mL), Dess-Martin periodinane (2.4 g, 5.69 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 50 minutes. The reaction was quenched with a saturated solution of sodium thiosulfate, extracted with ethyl acetate, washed with sodium bicarbonate, brine, and dried over magnesium sulfate. After removal of solvent, the residue was dried over vacuum to provide the compound as a yellow solid (132, 0.92 g, 93%).

Workup

customThe reaction was quenched with a saturated solution of sodium thiosulfate
extractionextracted with ethyl acetate
washwashed with sodium bicarbonate, brine
dry with materialdried over magnesium sulfate
customAfter removal of solvent
customthe residue was dried over vacuum

Sources & evidence

ORD record: ord-98da83649c104f92bc4e8c7dc16bece0
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872018B2

Reaction notes

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