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Cesium carbonate → 2-(4-(6-(Benzyloxy)-4-ethoxypyridin-3-yl)-3-fluorophenyl)acetamide

HRID 1050052
Notes
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Reaction equation

HRID 1050052 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:17][C:18]([NH2:20])=[O:19])[CH:5]=[CH:6][C:7]=1B1OC(C)(C)C(C)(C)O1.[CH2:21]([O:28][C:29]1[CH:34]=[C:33]([O:35][CH2:36][CH3:37])[C:32](I)=[CH:31][N:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:21]([O:28][C:29]1[N:30]=[CH:31][C:32]([C:7]2[CH:6]=[CH:5][C:4]([CH2:17][C:18]([NH2:20])=[O:19])=[CH:3][C:2]=2[F:1])=[C:33]([O:35][CH2:36][CH3:37])[CH:34]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 904161632-[3-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]acetamideHCID 904176602-(Benzyloxy)-4-ethoxy-5-iodopyridine

Product 1

HCID 904164292-(4-(6-(Benzyloxy)-4-ethoxypyridin-3-yl)-3-fluorophenyl)acetamideYield 100%

Reagents, catalysts & solvents 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide (100 mg, 0.358 mmol), 2-(benzyloxy)-4-ethoxy-5-iodopyridine (127 mg, 0.358 mmol), PdCl2(dppf) (26.2 mg, 0.036 mmol) and Cs2CO3 (233 mg, 0.717 mmol) in 1,4-dioxane (6 mL) and H2O (2 mL) was stirred at 110° C. for 15 min. After LCMS analysis showed the starting material had disappeared, the solvent was removed in vacuo. The residue was dissolved in EA (40 mL) and washed with H2O (20 mL) and brine (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified by preparative TLC (PE/EA=1/1) to yield 2-(4-(6-(benzyloxy)-4-ethoxypyridin-3-yl)-3-fluorophenyl)acetamide (20 mg, 0.358 mmol, 14.8% yield): 1H NMR (400 MHz, CD3OD) δ 7.87 (s, 1H), 7.56-7.43 (m, 2H), 7.43-7.22 (m, 4H), 7.21-7.11 (m, 2H), 6.50 (s, 1H), 5.38 (s, 2H), 4.13 (m, 2H), 3.58 (s, 2H), 1.32 (t, J=6.8 Hz, 3H); ES-LCMS m/z 381.1 (M+H).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in EA (40 mL)
  3. washwashed with H2O (20 mL) and brine (20 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by preparative TLC (PE/EA=1/1)

Sources & evidence

ORD record
ord-98e8f0834d014772a6d6d7e72f21c4b8
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09382238B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes