1,4-Dioxane → 4-[(2,4-Dimethoxy-benzyl)-methyl-amino]-2-fluoro-N-thiazol-2-yl-benzenesulfonamide

HRID 1644632Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[C:4]([F:17])[CH:3]=1.CC(C)([O-])C.[Na+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1.[CH3:72][O:73][C:74]1[CH:82]=[C:81]([O:83][CH3:84])[CH:80]=[CH:79][C:75]=1[CH2:76][NH:77][CH3:78]>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]>[CH3:72][O:73][C:74]1[CH:82]=[C:81]([O:83][CH3:84])[CH:80]=[CH:79][C:75]=1[CH2:76][N:77]([CH3:78])[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[C:4]([F:17])[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Into a vial was added the [B] 4-bromo-2-fluoro-N-thiazol-2-yl-benzenesulfonamide (170 mg, 0.00050 mol), sodium tert-butoxide (117 mg, 0.00121 mol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (18 mg, 0.000030 mol), Tris(dibenzylideneacetone)dipalladium(0) (9.3 mg, 0.000010 mol) and 1,4-dioxane (1.58 mL, 0.0202 mol). Argon was bubbled for 15 minutes. Into the reaction was added the [2,4-dimethoxy-benzyl)-methyl-amine (110 mg, 0.00061 mol) and the reaction mixture was heated at 100° C. overnight. The reaction mixture was cooled to room temperature then filtered over Celite. The filtrate was concentrated to give the crude compound as a yellow solid that was used in the next step without purification.

Workup

customArgon was bubbled for 15 minutes
temperatureThe reaction mixture was cooled to room temperature
filtrationthen filtered over Celite
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-a84de43490e343aa99edab0487d675f6
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124610B2

Reaction notes

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