Diisopropylethylamine → (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(tetrahydro-thiopyran-4-yl)-amine

HRID 1257664Notes

Reaction equation

HRID 1257664 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[C:18](Cl)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1.CCN(C(C)C)C(C)C>CC(O)C.CCOC(C)=O>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[C:18]([NH:29][CH:26]4[CH2:27][CH2:28][S:23][CH2:24][CH2:25]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 418807Tetrahydrothiopyran-4-ylamineHCID 583947741-(benzenesulfonyl)-4-chloro-5-nitro-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 67346464(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(tetrahydro-thiopyran-4-yl)-amineYield 86%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (0.50 g, 1.50 mmol) and tetrahydro-thiopyran-4-ylamine (0.19 g, 1.60 mmol) and DIEA (0.52 mL, 3.00 mmol) in IPA (4 mL) was heated in a microwave reactor at 120° C. for 10 minutes. The mixture was diluted with EtOAc, washed with water, brine, dried over sodium sulfate and then purified by column chromatography on silica gel (gradient: 0 to 30% ethyl acetate/heptane) to afford (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(tetrahydro-thiopyran-4-yl)-amine (0.53 g, 86%). 1H NMR (400 MHz, CDCl3) δ 9.18-9.03 (m, 2H), 8.26-8.12 (m, 2H), 7.70-7.46 (m, 4H), 6.65 (d, J=4.2 Hz, 1H), 4.07-3.91 (m, 1H), 2.88-2.70 (m, 4H), 2.49-2.34 (m, 2H), 2.05-1.76 (m, 2H).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulfate
  3. custompurified by column chromatography on silica gel (gradient: 0 to 30% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-0430a5f1ecad40a0806f6bddb2b5d199
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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