Iodine → HCID 22477267, compound

HRID 549040Notes

Reaction equation

[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C([Li])CCC.[I:25]I>O1CCCC1>[I:25][C:11]1[N:10]([S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:19])=[CH:6][CH:5]=2)(=[O:9])=[O:8])[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[CH:12]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [54.4 g, Reference Example 9(a)] in dry tetrahydrofuran (1200 mL) cooled to −78° C., was treated with a solution of butyllithium in hexanes (2.5M, 92 mL) over a 20 minute period. The solution was maintained at −78° C. for 30 minutes, then a solution of iodine (101 g) in tetrahydrofuran (600 mL) was added until the iodine colour persisted (ca. 300 mL). The mixture was allowed to warm slowly to ambient temperature and the solvent removed under vacuo. The residue was partitioned between ethyl acetate (1000 mL) and water (500 mL) and the aqueous layer was extracted twice with ethyl acetate (500 mL). The combined organics were combined, dried over sodium sulfate and removed under reduced pressure to give a yellow solid which was triturated with diethyl ether to give the title compound (79.6 g) as a pale yellow solid, m.p. 105-107° C. MS: 399 (MH+).

Workup

temperatureto warm slowly to ambient temperature
customthe solvent removed under vacuo
customThe residue was partitioned between ethyl acetate (1000 mL) and water (500 mL)
extractionthe aqueous layer was extracted twice with ethyl acetate (500 mL)
dry with materialdried over sodium sulfate
customremoved under reduced pressure
customto give a yellow solid which
customwas triturated with diethyl ether

Sources & evidence

ORD record: ord-6cb9331eecb3423e80134dcc228df250
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943616B2

Reaction notes

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