HCID 21942656, compound → HCID 66705649, compound

HRID 425341Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:11]2[N:12]([S:22]([N:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])[CH:13]=[C:14]([CH2:16][C:17]([CH3:21])([CH3:20])[CH2:18][CH3:19])[N:15]=2)[OH:10])=[CH:4][CH:3]=1.[F:28][C:29]1[CH:30]=[CH:31][C:32]([Sn](C)(C)C)=[N:33][CH:34]=1>COCCOC.C(OCC)(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:20][C:17]([CH3:21])([CH2:18][CH3:19])[CH2:16][C:14]1[N:15]=[C:11]([CH:9]([OH:10])[CH2:8][C:5]2[CH:6]=[CH:7][C:2]([C:32]3[CH:31]=[CH:30][C:29]([F:28])=[CH:34][N:33]=3)=[CH:3][CH:4]=2)[N:12]([S:22]([N:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])[CH:13]=1

Participants

Conditions

Temperature: 95 °C

Procedure

Palladium tetrakis(triphenylphosphine) (16 mg, 0.01 mmol) was added to a degassed, ambient temperature solution of 2-[2-(4-bromophenyl)-1-hydroxyethyl]-4-(2,2-dimethylbutyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (65 mg, 0.14 mmol) and 5-fluoro-2-(trimethylstannyl)pyridine (solution from the previous step containing 1.7 mmol) in 1,2-dimethoxyethane (10 mL). After stirring at 95° C. for 8 h, the reaction mixture was diluted with ethyl acetate and washed with water, dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-80% ethyl acetate/hexane afforded 4-(2,2-dimethylbutyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-hydroxyethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide.

Workup

washwashed with water
dry with materialdried (magnesium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8d7e188d47c542bb867d1678551c7554
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106070B2

Reaction notes

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