Potassium Hydroxide → 1-[4-chloro-3-(4,6-dichloro-pyridin-3-yl)-benzenesulfonyl]-2,3,4,5-tetrahydro-1H-1-benzazepine

HRID 2382683Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([S:9]([N:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].O.[Cl:24][C:25]1[CH:30]=[C:29]([Cl:31])[C:28](B(O)O)=[CH:27][N:26]=1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[OH-].[K+]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([S:9]([N:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:3][C:2]=1[C:28]1[CH:27]=[N:26][C:25]([Cl:24])=[CH:30][C:29]=1[Cl:31]

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 1-(3-bromo-4-chloro-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine, 2,4-dichloropyridine-5-boronic acid hydrate, tri-t-butylphosphonium tetrafluoroborate and tris(dibenzylideneacetone)dipalladium(0) in THF (0.73 mL) was added potassium hydroxide aqueous solution (0.05 g in 0.18 mL water). The suspension was bubbled with N2 for 5 min and then heated at 50° C. for 12 hrs. This mixture was cooled to it and concentrated. The residue was purified by silica gel column chromatography eluting with (hexanes/ethyl acetate, 20/1) to yield 1-[4-chloro-3-(4,6-dichloro-pyridin-3-yl)-benzenesulfonyl]-2,3,4,5-tetrahydro-1H-1-benzazepine 5-1 (9 mg, 8.7% yield). MS: 467 (M+H)+; tR=9.95 min (method 2).

Workup

customThe suspension was bubbled with N2 for 5 min
temperatureThis mixture was cooled to it
concentrationconcentrated
customThe residue was purified by silica gel column chromatography
washeluting with (hexanes/ethyl acetate, 20/1)

Sources & evidence

ORD record: ord-7de34dcd08a446a7bece118e404059d2
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263588B2

Reaction notes

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