HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1644632
Notes
Print preview

Reaction equation

HRID 1644632 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 312751,4-DioxaneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 2416536[(2,4-Dimethoxyphenyl)methyl](methyl)amineHCID 23676156Sodium t-butoxideHCID 251383534-Bromo-2-fluoro-N-thiazol-2-yl-benzenesulfonamide

Product 1

HCID 57551197
4-[(2,4-Dimethoxy-benzyl)-methyl-amino]-2-fluoro-N-thiazol-2-yl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

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

  1. customArgon was bubbled for 15 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthen filtered over Celite
  4. 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

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes