Dimethylformamide → 6-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 1025640Notes

Reaction equation

[O:1]=[S:2]1(=[O:27])[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[C:12]3[N:14]([Si](C(C)C)(C(C)C)C(C)C)[CH:15]=[CH:16][C:11]3=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[CH3:28][N:29](C=O)C.ClS(N=C=O)(=O)=O.CCOC(C)=O>C(#N)C>[O:27]=[S:2]1(=[O:1])[CH2:3][CH2:4][N:5]([C:8]2[N:13]=[C:12]3[NH:14][CH:15]=[C:16]([C:28]#[N:29])[C:11]3=[CH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

Conditions

Temperature: -20 °C

Procedure

In a 25 mL round-bottomed flask 6-(1,1-Dioxo-1lambda*6*-thiomorpholin-4-yl)-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (322 mg, 790 μmol, Eq: 1.00) was combined with DMF (11.9 ml) to give a colorless solution. The reaction mixture was cooled to −20° C. and stirred for 5 min. Chlorosulfonyl isocyanate (335 mg, 206 μl, 2.37 mmol, Eq: 3) in acetonitrile (11.9 ml) was added dropwise and the resultant cooled reaction was stirred at −20° C. and stirred for 3 hrs The reaction mixture was poured into 25 mL EtOAc and washed with sat NaCl (3×20 mL). After evaporation, crude material was purified by flash chromatography (silica gel, 12 g, 5% to 10% MeOH in DCM) to obtain 6-(1,1-dioxo-1lambda*6*-thiomorpholin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (122 mg, 56%).

Workup

customto give a colorless solution
temperaturethe resultant cooled
customreaction
stirringwas stirred at −20° C.
stirringstirred for 3 hrs The reaction mixture
washwashed
customAfter evaporation, crude material
customwas purified by flash chromatography (silica gel, 12 g, 5% to 10% MeOH in DCM)

Sources & evidence

ORD record: ord-697fd4c1eb7a4642a459a84d1f3212c0
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729078B2

Reaction notes

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