Potassium Carbonate → HCID 67540148, compound

HRID 1192393Notes

Reaction equation

HRID 1192393 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11](B2OC(C)(C)C(C)(C)O2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N1CCC(=O)CC1)=O)(C)(C)C.C([O-])([O-])=O.[K+].[K+].[C:43]1([S:49]([N:52]2[C:56]3=[N:57][CH:58]=[CH:59][C:60](Cl)=[C:55]3[CH:54]=[CH:53]2)(=[O:51])=[O:50])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:60]2[CH:59]=[CH:58][N:57]=[C:56]3[N:52]([S:49]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)(=[O:50])=[O:51])[CH:53]=[CH:54][C:55]=23)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 50602241-(Benzenesulfonyl)-4-chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 67540148HCID 67540148, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a nitrogen flushed flask containing 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (prepared from tert-butyl-4-oxopiperidine-1-carboxylate according to the literature: Eastwood, P. R. (2000), Tetrahedron Lett., 3705-3708. 127 mg, 0.410 mmol), K2CO3 (142 mg, 1.02 mmol) and dichloro[1,1′-bis(diphenylphosphino)-ferrocene]palladium(H)dichloromethane adduct (17 mg, 0.020 mmol) was added a solution of 1-Benzenesulfonyl-4-chloro-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.342 mmol) in DMF (3 mL). The mixture was heated at 80° C. for 36 hours. The mixture was cooled to room temperature and partitioned between EtOAc and water. The combined organic layers were washed with saturated aqueous NaHCO3 and brine, dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexanes:EtOAc (2:1) to give 4-(1-Benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.068 g, 45%) as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 8.37 (d, J=5.2 Hz, 1H), 8.20 (d, J=8.0 Hz, 2H), 7.73 (d, J=4.0 Hz, 1H), 7.56 (m, 1H), 7.49 (m, 2H), 7.03 (d, J=5.2 Hz, 1H), 6.73 (d, J=4.0 Hz, 1H), 6.14 (br s, 1H), 4.12 (m, 2H), 3.65 (m, 2H), 2.55 (m, 2H), 1.50 (s, 9H). LCMS (APCI+) m/z 440 [M+H]+; Rt=3.84 min.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between EtOAc and water
  3. washThe combined organic layers were washed with saturated aqueous NaHCO3 and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with hexanes:EtOAc (2:1)

Sources & evidence

ORD record
ord-d2ee6b26555741eb89ecac8b3d991f83
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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