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Cesium fluoride → HCID 59457671, compound

HRID 1711117
Notes
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Reaction equation

HRID 1711117 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:28]=[CH:27][C:12]([CH2:13][N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)=[CH:11][CH:10]=2)O1.[F:30][C:31]1[CH:47]=[C:46]([N+:48]([O-:50])=[O:49])[CH:45]=[CH:44][C:32]=1[O:33][C:34]1[CH:39]=[CH:38][N:37]=[C:36]2[CH:40]=[C:41](I)[S:42][C:35]=12.[F-].[Cs+].C([O-])(O)=O.[Na+]>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC.O>[F:30][C:31]1[CH:47]=[C:46]([N+:48]([O-:50])=[O:49])[CH:45]=[CH:44][C:32]=1[O:33][C:34]1[CH:39]=[CH:38][N:37]=[C:36]2[CH:40]=[C:41]([C:9]3[CH:28]=[CH:27][C:12]([CH2:13][N:14]4[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]4)=[CH:11][CH:10]=3)[S:42][C:35]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 25953Cesium fluorideHCID 516892Sodium BicarbonateHCID 53216820tert-Butyl 4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl)piperazine-1-carboxylateHCID 594576617-(2-Fluoro-4-nitrophenoxy)-2-iodothieno[3,2-b]pyridine

Product 1

HCID 59457671HCID 59457671, compoundYield 50.3%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 452 (22.36 g, 26.6 mmol), iodide 408 (7.904 g, 19.0 mmol), CsF (8.658 g, 57 mmol), NaHCO3 (4.788 g, 57 mmol) and Pd(PPh3)4 (2.195 g, 1.9 mmol) were combined with a mixture of H2O (25 mL) and DME (100 mL) which was with nitrogen for a half-an-hour and heated to reflux overnight. It was then was cooled to RT, diluted with EtOAc (200 ml), washed with aqueous NaHCO3 (50 mL) and brine (50 mL), and concentrated. The residue was purified by flash column chromatography (eluent pure EtOAc to 5% MeOH/EtOAc) followed by trituration with EtOAc/ether, to produce compound 453 as an off-white solid (5.4 g, 50% yield). LCMS: 565 (M+H)+.

Workup

  1. waitwas with nitrogen for a half-an-hour
  2. temperatureheated
  3. temperatureto reflux overnight
  4. washwashed with aqueous NaHCO3 (50 mL) and brine (50 mL)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (eluent pure EtOAc to 5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-defc9140296844cdb4df74a730f2b894
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07790729B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes