Sodium Bicarbonate → HCID 66632320, compound

HRID 1629912Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C:8]2[CH:17]=[C:16](B(O)O)[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:7]=1.C1(S([N:31]2[C:35]3=[CH:36][N:37]=[CH:38][CH:39]=[C:34]3[C:33](I)=[CH:32]2)(=O)=O)C=CC=CC=1.[C:41](=O)([OH:43])[O-:42].[Na+]>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH:41]([OH:43])=[O:42].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C:8]2[CH:17]=[C:16]([C:33]3[C:34]4[C:35](=[CH:36][N:37]=[CH:38][CH:39]=4)[NH:31][CH:32]=3)[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A slurry of 363 mg (1.20 mmol) 2-(5-chloro-2-fluoro-phenyl)-[1,8]naphthyridine-4-boronic acid, 384 mg (1.00 mmol) 1-benzenesulfonyl-3-iodo-1H-pyrrolo[2,3-c]pyridine (synthesis described in WO2006/052568) and 111 mg (1.32 mmol) sodium bicarbonate in 2 ml DMF and 1 ml water was heated to 80° C. under nitrogen. Then 41 mg (0.05 mmol) bis-(triphenylphosphine)-palladium(II)-chloride were added. The reaction mixture was stirred for 2 days at 90° C. Water was then added to the reaction mixture and the resulting precipitate was filtered off. The residue was purified by preparative HPLC yielding 2-(5-chloro-2-fluoro-phenyl)-4-(1H-pyrrolo[2,3-c]pyridin-3-yl)-[1,8]naphthyridine formate as colourless solid; HPLC-MS: 1.57 min, [M+H] 375.

Workup

filtrationthe resulting precipitate was filtered off
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-eed9388cf2484a2e8fc3c268ddc5917a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791113B2

Reaction notes

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