Sodium Carbonate → HCID 58626166, compound

HRID 1161686Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[CH:3]=1.[C:26]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)(=[O:28])[CH3:27].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.O>[N:8]1([C:6]2[N:7]=[C:2]([C:33]3[CH:34]=[C:29]([C:26](=[O:28])[CH3:27])[CH:30]=[CH:31][CH:32]=3)[CH:3]=[C:4]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[N:5]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

Conditions

Temperature: 30 °C

Procedure

To a mixture of compound (6-chloro-2-morpholin-4-yl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine (0.3 g, 0.8 mmol) and 3-acetyl benzene boronic acid (0.13 g, 0.79 mmol) in DMF (10 mL) was added palladium tetrakis triphenyl phosphine (0.027 g, 0.023 mmol) and 2M Na2CO3 soln (0.67 g, 6.32 mmol) at room temperature. The reaction mixture was then heated for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to temperature in the range of 20-40° C., diluted with water, extracted with ethyl acetate (3×10 mL). Combined organic layers were concentrated and the residue was purified by column chromatography using 15% ethylacetate in pet-ether to afford the desired compound (0.18 g, 49%) as a brown solid.

Workup

temperatureThe reaction mixture was then heated for 12 hours under nitrogen atmosphere
extractionextracted with ethyl acetate (3×10 mL)
concentrationCombined organic layers were concentrated
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-78db0ce2ae12428fbbf27af98489f5fc
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820654B2

Reaction notes

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