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Cesium carbonate → 7-(3-Methylpyridin-2-yl)-n-(5-(trifluoromethyl)pyrazin-2-yl)-[1,8]naphthyridin-4-amine

HRID 1724878
Notes
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Reaction equation

HRID 1724878 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=1)=[N:7]2.[NH2:19][C:20]1[CH:25]=[N:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:18][C:17]1[C:12]([C:6]2[N:7]=[C:8]3[C:3]([C:2]([NH:19][C:20]4[CH:25]=[N:24][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:22][N:21]=4)=[CH:11][CH:10]=[N:9]3)=[CH:4][CH:5]=2)=[N:13][CH:14]=[CH:15][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 133411155-(Trifluoromethyl)pyrazin-2-amineHCID 575610685-Chloro-2-(3-methylpyridin-2-yl)-1,8-naphthyridine

Product 1

HCID 575611327-(3-Methylpyridin-2-yl)-n-(5-(trifluoromethyl)pyrazin-2-yl)-[1,8]naphthyridin-4-amine

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Heat a mixture of 5-chloro-2-(3-methylpyridin-2-yl)-[1,8]naphthyridine (51 mg, 0.2 mmol), 2-amino-5-trifluoromethylpyrazine (42.0 mg, 0.25 mmol), xantphos (11.6 mg, 0.02 mmol); Pd2(dba)3 (18.3 mg, 0.02 mmol)and Cs2CO3 (130 mg, 0.4 mmol) in dioxane (2.0 mL) at 100° C. for 20 hours. Cool the mixture, concentrate under vacuum, dilute with EtOAc/water (5.0 mL each), filter through celite, wash celite with EtOAc (2×5 mL) and dry the combined organic layers with MgSO4. Filter the dried extract and concentrate under vacuum to afford the crude product. Purify by preparative TLC using 2% MeOH/EtOAc as eluent to afford the title compound as a yellow solid. 1H NMR (400 MHZ, DMSO-D6) δ 10.6 (s, 1H), 9.04 (d, 1H, J=2.1 Hz), 9.0 (s,1H), 8.77 (s, 2H), 8.59 (d, 1H, J=1.6 Hz), 8.4 (s, 1H), 8.20 (d, 1H, J=2.2 Hz), 7.81(d, 1H, J=1.9 Hz), 7.42 (dd, 1H), 2.65 (s, 3H). MS=383.11 (M+H).

Workup

  1. temperatureHeat
  2. temperatureCool the mixture
  3. concentrationconcentrate under vacuum
  4. additiondilute with EtOAc/water (5.0 mL each)
  5. filtrationfilter through celite
  6. washwash celite with EtOAc (2×5 mL)
  7. dry with materialdry the combined organic layers with MgSO4
  8. filtrationFilter the dried
  9. extractionextract
  10. concentrationconcentrate under vacuum
  11. customto afford the crude product
  12. customPurify by preparative TLC

Sources & evidence

ORD record
ord-d0897971a9e14a48a4df4dced3b13f44
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07488740B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes