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Cesium carbonate → HCID 59369338, compound

HRID 1689827
Notes
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Reaction equation

HRID 1689827 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH:4]([O:8][CH2:9][C:10]2[C:11]([C:18]3[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:25])=[N:12][O:13][C:14]=2[CH:15]2[CH2:17][CH2:16]2)[CH2:3][CH2:2]1.Br[C:27]1[CH:39]=[CH:38][C:30]2[C:31]([C:34]([O:36][CH3:37])=[O:35])=[N:32][S:33][C:29]=2[CH:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>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].C1(C)C(C)=CC=CC=1>[CH:15]1([C:14]2[O:13][N:12]=[C:11]([C:18]3[C:19]([Cl:25])=[CH:20][CH:21]=[CH:22][C:23]=3[Cl:24])[C:10]=2[CH2:9][O:8][CH:4]2[CH2:5][CH2:6][CH2:7][N:1]([C:27]3[CH:39]=[CH:38][C:30]4[C:31]([C:34]([O:36][CH3:37])=[O:35])=[N:32][S:33][C:29]=4[CH:28]=3)[CH2:2][CH2:3]2)[CH2:16][CH2:17]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 593693374-((Azepan-4-yloxy)methyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazoleHCID 66906285Methyl 6-bromobenzo[d]isothiazole-3-carboxylate

Product 1

HCID 59369338HCID 59369338, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

To an oven dried flask purged with argon, add 4-((azepan-4-yloxy)methyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol (0.51 g, 1.34 mmol), methyl 6-bromobenzo[d]isothiazole-3-carboxylate (0.30 g, 1.10 mmol), cesium carbonate (0.51 g, 1.56 mmol), X-Phos (0.04 g, 0.084 mmol), xylene (10 ml) and Pd2(dba)3 (0.025 g, 0.028 mmol). Purge the mixture with argon and heat to 130° C. until the starting materials are consumed as confirmed by TLC. Cool the reaction mixture to room temperature, filter through celite and concentrate in vacuo. The crude product is purified by flash chromatography on silica gel eluting with 6:4 hexane/ethyl acetate to give 0.30 g (47.0%) of the title compound as an off white solid. ES/MS m/z 571.11 (M+1).

Workup

  1. customTo an oven dried flask
  2. custompurged with argon
  3. customPurge the mixture with argon
  4. customare consumed
  5. temperatureCool the reaction mixture to room temperature
  6. filtrationfilter through celite
  7. concentrationconcentrate in vacuo
  8. customThe crude product is purified by flash chromatography on silica gel eluting with 6:4 hexane/ethyl acetate

Sources & evidence

ORD record
ord-acb45ab07e7b4c1dba1d4951e8ea2eaf
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08153624B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes