Cesium carbonate → HCID 58362628, compound

HRID 2361510Notes

Reaction equation

HRID 2361510 reaction equation
[N:1]1[C:2]2[N:3]([C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)[CH:4]=[CH:5][C:6]=1[C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[N:11][CH:12]=1.CC1C=CC(S(O[CH2:32][CH2:33][CH2:34][F:35])(=O)=O)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN1C(=O)CCC1.CCOC(C)=O>[F:35][CH2:34][CH2:33][CH2:32][O:13][C:10]1[N:11]=[CH:12][C:7]([C:6]2[CH:5]=[CH:4][N:3]3[C:14]4[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=4[N:16]=[C:2]3[N:1]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 63667743-Fluoroprop-1-yl toluene-4-sulphonateHCID 178515870HCID 178515870, compound

Product 1

HCID 58362628HCID 58362628, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To 5-(benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)pyridin-2-ol (8 mg, 0.03 mmol), and 3-fluoropropyl 4-methylbenzenesulfonate (21 mg, 0.09 mmol) in 0.3 mL of NMP was added Cs2CO3 (15 mg, 0.045 mmol). The reaction was stirred at rt for 4 h and diluted with EtOAc (10 mL). The mixture was washed with water (3×10 mL) and dried over MgSO4 and concentrated under reduced pressure. The residue was purified by reversed phase HPLC (water/MeCN with TFA buffer) to afford 2-(6-(3-fluoropropoxy)pyridin-3-yl)benzo[4,5]imidazo[1,2-a]pyrimidine as a off-white solid (3 mg, 31%). 1H NMR (400 MHz, methanol-d4): δ 9.79 (d, J=7.2 Hz, 1H), 8.66 (d, J=2.8 Hz, 1H), 8.69 (dd, J=8.8, 2.8 Hz, 1H), 8.40 (d, J=8.8 Hz, 1H), 8.29 (d, J=7.2 Hz, 1H), 7.90-7.82 (m, 2H), 7.72 (m, 1H), 7.04 (d, J=8.8 Hz, 1H), 4.68 (t, J=5.6 Hz, 1H), 4.57 (t, J=6.4 Hz, 2H), 4.56 (t, J=5.6 Hz, 1H), 2.30-2.16 (m, 2H); MS (ESI) m/z [M+H]+323.

Workup

  1. washThe mixture was washed with water (3×10 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by reversed phase HPLC (water/MeCN with TFA buffer)

Sources & evidence

ORD record
ord-73c20d117e7b4e2bbe8e47fb3c452363
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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