5-nitro-1-(phenylsulfonyl)-N-(tetrahydro-2H-pyran-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-amine → 1-(phenylsulfonyl)-N4-(tetrahydro-2H-pyran-3-yl)-1H-pyrrolo[2,3-b]pyridine-4,5-diamine

HRID 1257658Notes

Reaction equation

HRID 1257658 reaction equation
[N+:1]([C:4]1[CH:9]=[N:8][C:7]2[N:10]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]=[CH:12][C:6]=2[C:5]=1[NH:22][CH:23]1[CH2:28][CH2:27][CH2:26][O:25][CH2:24]1)([O-])=O>C(OCC)(=O)C.[Pd]>[C:16]1([S:13]([N:10]2[C:7]3=[N:8][CH:9]=[C:4]([NH2:1])[C:5]([NH:22][CH:23]4[CH2:28][CH2:27][CH2:26][O:25][CH2:24]4)=[C:6]3[CH:12]=[CH:11]2)(=[O:14])=[O:15])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 1

HCID 673447495-nitro-1-(phenylsulfonyl)-N-(tetrahydro-2H-pyran-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-amine

Product 1

HCID 673439541-(phenylsulfonyl)-N4-(tetrahydro-2H-pyran-3-yl)-1H-pyrrolo[2,3-b]pyridine-4,5-diamineYield 94.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-nitro-1-(phenylsulfonyl)-N-(tetrahydro-2H-pyran-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-amine (11.7 g, 29.1 mmol) in ethyl acetate (400 mL) was added 10% palladium on carbon (3.0 g, 3.0 mmol). The mixture was stirred at ambient temperature under an atmosphere of hydrogen for 16 h. Filtration and concentration afforded 10.2 g (94.2%) of 1-(phenylsulfonyl)-N4-(tetrahydro-2H-pyran-3-yl)-1H-pyrrolo[2,3-b]pyridine-4,5-diamine. LCMS (Method E, ESI): RT=1.16 min, m+H=373.3; 1H NMR (400 MHz, CDCl3) δ 8.25-7.99 (m, 2H), 7.84 (s, 1H), 7.61-7.35 (m, 4H), 6.58 (d, J=4.2 Hz, 1H), 5.04 (t, J=12.8 Hz, 1H), 4.02-3.82 (m, 2H), 3.80-3.55 (m, 2H), 3.47 (dd, J=11.1, 6.1 Hz, 1H), 2.86 (s, 2H), 2.11-1.93 (m, 1H), 1.80 (dtd, J=14.6, 7.2, 3.7 Hz, 1H), 1.74-1.51 (m, 3H).

Workup

  1. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-38a660cd9bc6492d88c478d53d886bd4
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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