Diisopropylethylamine → (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-bicyclo[2.2.1]hept-2-yl-amine

HRID 1257609Notes

Reaction equation

HRID 1257609 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.[CH:23]12[CH2:29][CH:26]([CH2:27][CH2:28]1)[CH2:25][CH:24]2[NH2:30].C(N(C(C)C)CC)(C)C>CC(O)C>[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:30][CH:24]4[CH2:25][CH:26]5[CH2:29][CH:23]4[CH2:28][CH2:27]5)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 98480Exo-2-bornanamineHCID 583947741-(benzenesulfonyl)-4-chloro-5-nitro-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 67343346(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-bicyclo[2.2.1]hept-2-yl-amineYield 98.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (0.92 g, 2.7 mmol), bicyclo[2.2.1]hept-2-ylamine (0.36 ml, 3.0 mmol), diisopropylethylamine (0.62 ml, 3.5 mmol) in propan-2-ol (12 ml) was heated at 110° C. in a microwave reactor for 20 min. The mixture was then cooled to 25° C. and was partitioned between water (200 ml) and EtOAc (2×200 ml). The combined organic layers were dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure. Purification of the resulting yellow oil by column chromatography on silica gel (gradient: 0 to 60% EtOAc in heptanes) afforded (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-bicyclo[2.2.1]hept-2-yl-amine (1.1 g, 98%) as a yellow solid. TLC: 50% EtOAc in heptanes; Rf=0.66). This material was used in the next step below without additional characterization.

Workup

  1. temperatureThe mixture was then cooled to 25° C.
  2. customwas partitioned between water (200 ml) and EtOAc (2×200 ml)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customPurification of the resulting yellow oil by column chromatography on silica gel (gradient: 0 to 60% EtOAc in heptanes)

Sources & evidence

ORD record
ord-f114f67c1a5c457aa097eb15c14998d8
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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