Ethanol → tert-butyl 1-(5-(5-(2-fluorophenyl)-1-tosyl-1H-pyrrolo[3,2-b]pyridin-3-yl)pyridin-3-yl)piperidin-4-ylcarbamate

HRID 1529345Notes

Reaction equation

HRID 1529345 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[C:14](I)=[CH:15][N:16]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:11]2=[CH:10][CH:9]=1.CC1(C)C(C)(C)OB([C:36]2[CH:37]=[C:38]([N:42]3[CH2:47][CH2:46][CH:45]([NH:48][C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52])[CH2:44][CH2:43]3)[CH:39]=[N:40][CH:41]=2)O1.C([O-])([O-])=O.[Na+].[Na+].CCO>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[C:14]([C:36]3[CH:37]=[C:38]([N:42]4[CH2:43][CH2:44][CH:45]([NH:48][C:49](=[O:55])[O:50][C:51]([CH3:53])([CH3:52])[CH3:54])[CH2:46][CH2:47]4)[CH:39]=[N:40][CH:41]=3)=[CH:15][N:16]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:11]2=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 67959870Tert-butyl 1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)piperidin-4-ylcarbamateHCID 679599075-(2-fluorophenyl)-3-iodo-1-tosyl-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 67960027tert-butyl 1-(5-(5-(2-fluorophenyl)-1-tosyl-1H-pyrrolo[3,2-b]pyridin-3-yl)pyridin-3-yl)piperidin-4-ylcarbamateYield 66.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 5-(2-fluorophenyl)-3-iodo-1-tosyl-1H-pyrrolo[3,2-b]pyridine (155 mg, 0.315 mmol), tert-butyl 1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)piperidin-4-ylcarbamate (222 mg, 0.551 mmol) Pd(PPh3)4 (36.4 mg, 0.031 mmol, Strem) and Na2CO3, 2.0 M (0.315 mL, 0.630 mmol) in Toluene (2 mL) and EtOH (2 mL) was capped, degassed and backfilled with argon. The reaction was heated to 100° C. After 18 h, the reaction was cooled to 23° C., diluted with EtOAc (75 mL) and washed with brine (50 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluent: 0-4% MeOH/DCM), affording tert-butyl 1-(5-(5-(2-fluorophenyl)-1-tosyl-1H-pyrrolo[3,2-b]pyridin-3-yl)pyridin-3-yl)piperidin-4-ylcarbamate (134 mg, 66%). MS (ESI, pos. ion) m/z: 642.4 (M+1).

Workup

  1. customdegassed
  2. temperaturethe reaction was cooled to 23° C.
  3. additiondiluted with EtOAc (75 mL)
  4. washwashed with brine (50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel chromatography (eluent: 0-4% MeOH/DCM)

Sources & evidence

ORD record
ord-80c9b9e55c6e4ec09d88820020687cd7
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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