Sodium Carbonate → HCID 10298257, compound

HRID 1839152Notes

Reaction equation

[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20](B3OC(C)(C)C(C)(C)O3)[CH:19]=2)[CH:8]=1)=[O:6])([CH3:3])[CH3:2].Br[C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=2)=[CH:36][CH:35]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:34]3[CH:35]=[CH:36][C:37]([C:40]4[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=4)=[CH:38][CH:39]=3)[CH:19]=2)[CH:8]=1)=[O:6])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of the boronate from Step 1, 3-(4-bromophenyl)pyridine from Step 2 (1.5 eq), [1,1′-bis (diphenylphosphino)ferrocene]dichloropalladium(II) (0.05 eq) and 2M aqueous sodium carbonate (5 eq) in N,N-dimethylformamide (7 ml/mmol) was stirred at 85° C. for 1 hour. After cooling, the mixture was partitioned between ethyl acetate and water. The crude product from the organic phase was chromatographed on silica gel eluting with a 7:3 mixture of ethyl acetate and methylene chloride to afford the N-Isopropyl-1-{3-[4-(pyridin-3-yl)phenyl]phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide compound as a solid.

Workup

temperatureAfter cooling
customthe mixture was partitioned between ethyl acetate and water
customThe crude product from the organic phase was chromatographed on silica gel eluting with a 7:3 mixture of ethyl acetate and methylene chloride

Sources & evidence

ORD record: ord-02596ebbfc924214bd685b87184a2b91
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677351B2

Reaction notes

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