Tetrahydrofuran → HCID 58063567, compound

HRID 2035714Notes

Reaction equation

HRID 2035714 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.I[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[N:17][N:18]([CH:20]3[CH2:26][CH2:25][C:24]4[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=4[N:22]([CH2:31][C:32]([F:35])([F:34])[F:33])[C:21]3=[O:36])[CH:19]=2)=[CH:11][C:10]=1[O:37][CH3:38].CC(C)([O-])C.[K+].C1COCC1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:38][O:37][C:10]1[CH:11]=[C:12]([C:15]2[N:16]=[N:17][N:18]([CH:20]3[CH2:26][CH2:25][C:24]4[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=4[N:22]([CH2:31][C:32]([F:35])([F:34])[F:33])[C:21]3=[O:36])[CH:19]=2)[CH:13]=[CH:14][C:9]=1[NH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 100093-AminopyridineHCID 634876Binap, (A+-)-HCID 23665647Potassium tert-butoxideHCID 66683035HCID 66683035, compound

Product 1

HCID 58063567HCID 58063567, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A suspension of pyridin-3-amine (3.48 mg, 0.037 mmol 3-[4-(4-iodo-3-methoxyphenyl)-1H-1,2,3-triazol-1-yl]-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (20 mg, 0.037 mmol), potassium tert-butoxide 1M in THF (36.9 μL, 0.037 mmol), BINAP (4.59 mg, 0.008 mmol), and palladium acetate (1.66 mg, 0.008 mmol) were combined in a μwave vial and dissolved in DMF (738 μl). The reaction was microwaved at 180° C. for 10 min. The reaction mixture was filtered, and the solvent was removed in vacuo. Analytically pure material was obtained by purification by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.05% Formic Acid. Lyophilisation afforded 3-{4-[3-methoxy-4-(pyridin-3-ylamino)phenyl]-1H-1,2,3-triazol-1-yl}-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Workup

  1. customThe reaction was microwaved at 180° C. for 10 min
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was removed in vacuo
  4. customAnalytically pure material was obtained by purification by preparative HPLC Reverse phase (C-18)
  5. washeluting with acetonitrile/water+0.05% Formic Acid

Sources & evidence

ORD record
ord-6c667677581d4d06bfed17e0f941e5de
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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