Iodine → HCID 22477267, compound

HRID 1765590Notes

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 water re-extracted with ethyl acetate (2×500 mL). The organic extracts 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.

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 water re-extracted with ethyl acetate (2×500 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-e0dd24ad88d14f49ba251f4293ca34bc
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07227020B2

Reaction notes

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