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Potassium Carbonate → 4-(4-Fluoro-phenyl)-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrole

HRID 533725
Notes
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Reaction equation

HRID 533725 reaction equation
Cl[C:2]1[C:10]2[C:9]3[CH2:11][NH:12][CH2:13][CH2:14][C:8]=3[NH:7][C:6]=2[N:5]=[CH:4][CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.CCOC(C)=O.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[C:10]3[C:9]4[CH2:11][NH:12][CH2:13][CH2:14][C:8]=4[NH:7][C:6]=3[N:5]=[CH:4][CH:3]=2)=[CH:18][CH:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 666779724-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrole

Product 1

HCID 468431424-(4-Fluoro-phenyl)-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrroleYield 29%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 218864351,4-Dioxane--water (1/1)SolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
100 °C

Procedure

4-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrole (100 mg, 0.48 mmol), 4-fluorophenylboronic acid (135 mg, 0.96 mmol), Pd(OAc)2 (5 mg, 0.02 mmol), S-Phos (20 mg, 0.05 mmol), and K2CO3 (266 mg, 1.93 mmol) were dissolved in dioxane/H2O (2.2 mL, 10/1, v/v), and stirred overnight at 100° C. The reaction mixture diluted with EtOAc/H2O, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude material was triturated with EtOAc, filtered, washed with EtOAc, and dried under vacuum to provide 6 (37 mg, 29% yield) as a tan solid. LC-MS (M+H=269, obsd.=269).

Workup

  1. filtrationfiltered through an Extrelut column
  2. washThe column was washed with EtOAc
  3. concentrationthe filtrate was concentrated
  4. customThe crude material was triturated with EtOAc
  5. filtrationfiltered
  6. washwashed with EtOAc
  7. customdried under vacuum

Sources & evidence

ORD record
ord-e34ebba37db2424d9cdffd525904dd65
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08853391B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes