Hydrochloric Acid → HCID 25230950, compound

HRID 2272940Notes

Reaction equation

HRID 2272940 reaction equation
Cl[C:2]1[S:10][C:9]2[C:8]([C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[O:12])=[N:7][C:6]([NH:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[N:5][C:4]=2[CH:3]=1.[C:26](P(C(C)(C)C)C(C)(C)C)(C)(C)[CH3:27].C(C([Sn])=C(CCCC)CCCC)CCC.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>O1CCCC1>[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([CH2:19][NH:18][C:6]2[N:7]=[C:8]([C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[O:12])[C:9]3[S:10][C:2]([CH:26]=[CH2:27])=[CH:3][C:4]=3[N:5]=2)[CH:21]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 46883208HCID 46883208, compoundHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 25230950HCID 25230950, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

A stirred solution of Example 5 (0.05 g, 0.13 mmol) in tetrahydrofuran (3 ml) at room temperature was treated with tris[di(benzylidene)acetone]palladium (0) (0.006 g, 0.0065 mmol), tri-tert-butylphosphine (0.01 ml, 0.04 mmol), tributylvinyltin (0.06 ml, 0.0.195 mmol), and caesium carbonate (0.046 g, 0.14 mmol). The mixture was heated to 140° C. for 20 min in a microwave reactor. The cooled reaction mixture was poured onto aqueous HCl (2.5M, 25 ml), washed with ethylacetate, and basified (pH9) using aqueous sodium hydroxide solution (5M). The aqueous phase was extracted with ethyl acetate (2×30 ml). Combined extracts were dried over sodium sulfate and reduced in vacuo. Silica gel (10 g) column chromatography (ethyl acetate) afforded the title compound as a yellow solid in 51% yield, >95% purity. LC-MS m/z=379.0 [M+H]+; RT=3.15; LC-MS method 1. 1H NMR: δH (400 MHz, D6-DMSO) 4.73 (2H, b), 5.57 (1H, d, J 10.5 Hz), 6.00 (1H, d, J 17.5 Hz), 7.06-7.14 (1H, m), 7.29-7.35 (3H, m), 7.79 (1H, d, J 8.0 Hz), 8.11-8.19 (2H, m), 8.43 (1H, d, J 4.5 Hz), 8.64 (1H, bd), 8.43-8.64 (1H, b)

Workup

  1. customThe cooled reaction mixture
  2. washwashed with ethylacetate, and basified (pH9)
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×30 ml)
  4. dry with materialCombined extracts were dried over sodium sulfate

Sources & evidence

ORD record
ord-d88ba0faf009454482eefda82438de59
Source dataset
uspto-grants-2015_09
Patent number
US09120807B2

Reaction notes

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