7-Chloro-2-iodothieno(3,2-b)pyridine → 6-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

HRID 1676393Notes

Reaction equation

HRID 1676393 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:14](=[O:15])[N:13]3[CH2:16][CH2:17][N:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:12]3=[N:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].Cl[C:26]1[CH:31]=[CH:30][N:29]=[C:28]2[CH:32]=[C:33]([I:35])[S:34][C:27]=12>CN(C1C=CN=CC=1)C.BrC1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:14](=[O:15])[N:13]3[CH2:16][CH2:17][N:18]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:12]3=[N:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:26]1[CH:31]=[CH:30][N:29]=[C:28]2[CH:32]=[C:33]([I:35])[S:34][C:27]=12

Participants

5

Reactant 2

HCID 177504007-Chloro-2-iodothieno(3,2-b)pyridineHCID 673463376-(3-fluoro-4-hydroxyphenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

Product 1

HCID 673468456-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7961BromobenzeneSolvent

Procedure

A mixture of 6-(3-fluoro-4-hydroxyphenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one (0.078 g, 0.186 mmol), 7-chloro-2-iodothieno[3,2-b]pyridine (0.050 g, 0.169 mmol; prepared according to the procedure of Ragan, J. A. Org. Proc. Res. 2003, 7, 676) and DMAP (0.021 g, 0.169 mmol) in bromobenzene (1.5 mL) under nitrogen was stirred at 150° C. for two days. The reaction was concentrated in vacuo to remove as much bromobenzene as possible and then purified directly by flash column chromatography, eluting with 30:1 CH2Cl2/MeOH. The product was obtained (35 mg; 36%) as a yellow solid. LRMS (APCI pos) m/e 583 (M+1).

Workup

  1. customprepared
  2. concentrationThe reaction was concentrated in vacuo
  3. customto remove as much bromobenzene as possible and
  4. customthen purified directly by flash column chromatography
  5. washeluting with 30:1 CH2Cl2/MeOH
  6. customThe product was obtained (35 mg; 36%) as a yellow solid

Sources & evidence

ORD record
ord-b91f38f2304e41f59d98ac96f778fc51
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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