Potassium Carbonate → HCID 59410234, compound

HRID 2382682Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][CH2:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.Br[C:32]1[C:33]([CH3:39])=[CH:34][C:35]([Cl:38])=[N:36][CH:37]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][CH2:14][CH2:13][CH2:12]2)(=[O:9])=[O:10])=[CH:4][C:3]=1[C:32]1[CH:37]=[N:36][C:35]([Cl:38])=[CH:34][C:33]=1[CH3:39]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-[4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzenesulfonyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (67 mg, 0.18 mmol), 5-bromo-2-chloro-4-picoline (45 mg, 0.22 mmol), Pd(PPh3)4 (11 mg, 0.01 mmol), K2CO3 (130 mg, 0.93 mmol) in 1,4-Dioxane (1 mL), was heated at 100° C. for 12 hrs. This mixture was cooled to rt and the solvent evaporated. The residue was purified by silica gel column chromatography eluted with (Hexanes/Ethyl acetate, 9/1) to yield 1-[4-chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-benzenesulfonyl]-2,3,4,5-tetrahydro-1H-1-benzazepine 4-1 (0.019 g, 23% yield). MS: 447 (M+H)+; tR=9.94 min (method 2).

Workup

temperatureThis mixture was cooled to rt
customthe solvent evaporated
customThe residue was purified by silica gel column chromatography
washeluted with (Hexanes/Ethyl acetate, 9/1)

Sources & evidence

ORD record: ord-2ffc190729c644558d3b8d65259cfbb5
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263588B2

Reaction notes

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