Dimethylformamide → tert-butyl 4-(1-{[3-(3-methoxypyrrolidin-1-yl)phenyl]sulfonyl}-1H-pyrrolo[3,2-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxylate

HRID 641883Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH:15]=2)=[CH:2]1.CN(C)C=O.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:38][O:39][CH:40]1[CH2:44][CH2:43][N:42]([C:45]2[CH:46]=[C:47]([S:51](Cl)(=[O:53])=[O:52])[CH:48]=[CH:49][CH:50]=2)[CH2:41]1>O1CCCC1>[CH3:38][O:39][CH:40]1[CH2:44][CH2:43][N:42]([C:45]2[CH:46]=[C:47]([S:51]([N:1]3[C:9]4[C:4](=[N:5][CH:6]=[CH:7][CH:8]=4)[C:3]([C:10]4[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH:15]=4)=[CH:2]3)(=[O:53])=[O:52])[CH:48]=[CH:49][CH:50]=2)[CH2:41]1

Participants

Conditions

Temperature: 5 °C

Procedure

Into a 1-Neck round-bottom flask tert-butyl 4-(1H-pyrrolo[3,2-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxylate (100 mg, 0.000334 mol) was stirred in tetrahydrofuran (3 mL, 0.04 mol) and N,N-dimethylformamide (3 mL, 0.04 mol) at 5° C. and 1.0 M of sodium bis(trimethylsilyl)amide in tetrahydrofuran (0.50 mL) was added. The reaction was stirred for 20 minutes at 5° C. 3-(3-Methoxypyrrolidin-1-yl)benzenesulfonyl chloride (138 mg, 0.000501 mol) in tetrahydrofuran (3 mL, 0.04 mol) was added by syringe at 5° C. and the reaction was stirred for 30 minutes. The reaction was extracted with ethyl acetate and was washed with water and brine. The solvent was rotovaped.

Workup

stirringthe reaction was stirred for 30 minutes
extractionThe reaction was extracted with ethyl acetate
washwas washed with water and brine

Sources & evidence

ORD record: ord-3ecbfcb2b566471eb470467e6eaacda1
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696229B2

Reaction notes

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