2-Methylthio-1-pyrroline → N-(3,4-dihydro-2H-pyrrol-5-yl)-4-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amine

HRID 576684Notes

Reaction equation

HRID 576684 reaction equation
[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][N:5]=[C:4]2[N:9]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:10]=[CH:11][C:3]=12.CS[C:23]1[CH2:24][CH2:25][CH2:26][N:27]=1>CC(O)C>[NH3:5].[N:27]1[CH2:26][CH2:25][CH2:24][C:23]=1[NH:8][C:7]1[C:2]([CH3:1])=[C:3]2[CH:11]=[CH:10][N:9]([S:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)(=[O:14])=[O:13])[C:4]2=[N:5][CH:6]=1

Participants

5

Reactant 2

HCID 122699262-Methylthio-1-pyrrolineHCID 671156214-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amine

Product 2

HCID 222AmmoniaYield 4%HCID 68160109N-(3,4-dihydro-2H-pyrrol-5-yl)-4-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amineYield 37.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amine, (775 mg, 2.7 mmol) and 5-(methylthio)-3,4-dihydro-2H-pyrrole (345 mg) in i-PrOH (14 mL) was heated at 105° C. for 3 days. The refluxed mixture was then cooled to room temperature and concentrated. Flash column chromatography (4-6% 7N NH3 in MeOH/DCM) yielded N-(3,4-dihydro-2H-pyrrol-5-yl)-4-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amine, (180 mg) 1H NMR (300 MHZ, CD3OD) δ: 8.10 (d, J=7.6 Hz, 2H), 7.89 (s, 1H), 7.75 (d, J=4.1 Hz, 1H), 7.63 (s, 1H), 7.54 (d, J=8.2 Hz, 2H), 6.77 (d, J=4.1 Hz, 1H), 2.63 (s, 2H), 2.09 (t, J=7.5 Hz, 3H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-0f0f4cdcf29e4923893be897f37e02aa
Source dataset
uspto-grants-2015_05
Patent number
US09040532B2

Reaction notes

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