Cesium carbonate → HCID 131735793, compound

HRID 2203683Notes

Reaction equation

HRID 2203683 reaction equation
[Si:1]([O:18][CH:19]1[CH2:24][CH:23]2[CH:21]([CH:22]2[C:25](=[O:32])[CH:26]=[C:27]([S:30][CH3:31])SC)[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:41]2[CH:42]=[C:43]([O:48][C:49]([F:52])([F:51])[F:50])[C:44]([NH2:47])=[N:45][CH:46]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>S1C=CC=C1C(O[Cu])=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].O1CCCC1.O>[NH2:47][C:44]1[N:45]=[CH:46][C:41](/[C:27](/[S:30][CH3:31])=[CH:26]\[C:25]([CH:22]2[CH:23]3[CH:21]2[CH2:20][CH:19]([O:18][Si:1]([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:24]3)=[O:32])=[CH:42][C:43]=1[O:48][C:49]([F:52])([F:50])[F:51]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 90286515HCID 90286515, compoundHCID 123702800HCID 123702800, compound

Product 1

HCID 131735793HCID 131735793, compoundYield 27.9%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 178526049HCID 178526049, compoundCatalystHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

A microwave vial charged with 1-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)-3,3-bis(methylthio)prop-2-en-1-one (2.0 g, 4.1 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoro-methoxy)-pyridin-2-amine (1.89 g, 6.23 mmol), ((thiophene-2-carbonyl)oxy)copper (1.58 g, 8.29 mmol), cesium carbonate (2.7 g, 8.3 mmol) and tetra(triphenylphosphine)palladium (0) (957 mg, 0.83 mmol) in 10:1 tetrahydrofuran/water (22 mL) was purged with nitrogen for 3 min. The reaction mixture was sealed and heated by microwave irradiation at 100° C. for 1.5 h. The reaction mixture was concentrated in vacuo, and the resulting residue was purified by flash column chromatography (40% ethyl acetate in petroleum ether) to provide product as a yellow oil (0.70 g, 26% yield). LCMS (ESI) [MH]+=613.1.

Workup

  1. customwas purged with nitrogen for 3 min
  2. customThe reaction mixture was sealed
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe resulting residue was purified by flash column chromatography (40% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-3689c6fc70e841658e98a84eab3ad58e
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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