Sodium Carbonate → HCID 59436032, compound

HRID 1802484Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([NH:11][C:12]2[C:21]3[CH:20]=[CH:19][NH:18][C:17](=[O:22])[C:16]=3[C:15]3[CH:23]=[C:24](B4OC(C)(C)C(C)(C)O4)[CH:25]=[CH:26][C:14]=3[N:13]=2)=[C:6]([Cl:36])[CH:5]=1)(=[O:3])[CH3:2].Br[C:38]1[N:39]=[C:40]([C:43]([OH:46])([CH3:45])[CH3:44])[S:41][CH:42]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([NH:11][C:12]2[C:21]3[CH:20]=[CH:19][NH:18][C:17](=[O:22])[C:16]=3[C:15]3[CH:23]=[C:24]([C:38]4[N:39]=[C:40]([C:43]([OH:46])([CH3:45])[CH3:44])[S:41][CH:42]=4)[CH:25]=[CH:26][C:14]=3[N:13]=2)=[C:6]([Cl:36])[CH:5]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-[(4-acetyl-2,6-dichlorophenyl)amino]-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c]-2,6-naphthyridin-1(2H)-one (135 mg, 0.26 mmol) in THF (4 mL) was added 2-(4-bromo-1,3-thiazol-2-yl)propan-2-ol (114 mg, 0.52 mmol), Pd(Ph3P)4 (60 mg, 0.05 mmol) and sodium carbonate (0.129 mL, 0.26 mmol, 2M in water). The reaction was heated to 80° C. for 16 h. The reaction was diluted with ethyl acetate and extracted with water. The organic layer was dried with sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound.

Workup

extractionextracted with water
dry with materialThe organic layer was dried with sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d899a5fb5a5945beadc4ece55949e2e6
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349865B2

Reaction notes

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