Iodoethane → tert-butyl 4-({6-[5-(1-ethyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-yl]pyrazin-2-yl}oxy)piperidine-1-carboxylate

HRID 1926654Notes

Reaction equation

HRID 1926654 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:20]=[N:21][NH:22][CH:23]=4)[CH:18]=[C:13]3[C:12]([C:24]3[N:29]=[C:28]([O:30][CH:31]4[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]4)[CH:27]=[N:26][CH:25]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[CH2:45][CH3:46].[H-].[Na+]>CN(C=O)C>[CH2:45]([N:22]1[CH:23]=[C:19]([C:17]2[CH:18]=[C:13]3[C:12]([C:24]4[N:29]=[C:28]([O:30][CH:31]5[CH2:32][CH2:33][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:35][CH2:36]5)[CH:27]=[N:26][CH:25]=4)=[CH:11][N:10]([S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:8])=[O:9])[C:14]3=[N:15][CH:16]=2)[CH:20]=[N:21]1)[CH3:46]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 57502444tert-butyl 4-({6-[1-(phenylsulfonyl)-5-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-yl]pyrazin-2-yl}oxy)piperidine-1-carboxylate

Product 1

HCID 68668858tert-butyl 4-({6-[5-(1-ethyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-yl]pyrazin-2-yl}oxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of tert-butyl 4-({6-[1-(phenylsulfonyl)-5-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-yl]pyrazin-2-yl}oxy)piperidine-1-carboxylate (0.075 g, 0.13 mmol) and iodoethane (11 pt, 0.14 mmol) in DMF (1.3 mL) at 0° C. was added sodium hydride (60% mineral oil dispersion; 6.0 mg, 0.15 mmol). The reaction mixture was stirred at 0° C. for 1 h then quenched with aqueous saturated sodium bicarbonate (5 mL). The reaction mixture was extracted with EtOAc (3×10 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography (EtOAc/Hexanes gradient) to afford tert-butyl 4-({6-[5-(1-ethyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-yl]pyrazin-2-yl}oxy)piperidine-1-carboxylate as a yellow oil. LRMS (ESI) calculated for C32H35N7O5S [M+H]+, 630.2; found 630.2.

Workup

  1. customthen quenched with aqueous saturated sodium bicarbonate (5 mL)
  2. extractionThe reaction mixture was extracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by silica gel chromatography (EtOAc/Hexanes gradient)

Sources & evidence

ORD record
ord-be13fb66d06d4810a82631cc0442e4d7
Source dataset
uspto-grants-2012_05
Patent number
US08183245B2

Reaction notes

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