Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 58466326, compound

HRID 335961Notes

Reaction equation

CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.[CH3:18][N:19]([CH3:43])[C:20]1[N:25]=[CH:24][C:23]2[O:26][C:27]3[C:32]([C:33]([CH3:35])(O)[C:22]=2[CH:21]=1)=[CH:31][C:30]([C:36]1[C:37]([F:42])=[N:38][CH:39]=[CH:40][CH:41]=1)=[CH:29][CH:28]=3.C(=O)(O)[O-].[Na+]>ClCCCl>[F:42][C:37]1[C:36]([C:30]2[CH:31]=[C:32]3[C:27](=[CH:28][CH:29]=2)[O:26][C:23]2[CH:24]=[N:25][C:20]([N:19]([CH3:18])[CH3:43])=[CH:21][C:22]=2[C:33]3=[CH2:35])=[CH:41][CH:40]=[CH:39][N:38]=1

Participants

Conditions

Temperature: 60 °C

Procedure

PPTS (0.082 g, 0.327 mmol) was added in one portion to a suspension of 3-(dimethylamino)-7-(2-fluoropyridin-3-yl)-5-methyl-5H-chromeno[2,3-c]pyridin-5-ol (0.23 g, 0.66 mmol) in DCE (8 mL) and the reaction was heated to 60° C. The resulting solution was stirred until judged complete by LC/MS. The solution was allowed to cool and then poured into saturated aqueous sodium bicarbonate. The layers were seperated and the aqueous layer was extracted with DCM and the combined organic extracts were washed with saturated aqueous sodium chloride and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to afford 7-(2-fluoropyridin-3-yl)-N,N-dimethyl-5-methylene-5H-chromeno[2,3-c]pyridin-3-amine which was used directly for the next reaction without further purification. MS m/z=334.2 [M+H].

Workup

temperatureto cool
customThe layers were seperated
extractionthe aqueous layer was extracted with DCM
washthe combined organic extracts were washed with saturated aqueous sodium chloride
dry with materialdried over sodium sulfate
filtrationThe solution was filtered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-58dbf9fe425e4d768e4cb66e83f55f94
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883782B2

Reaction notes

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