Cesium carbonate → HCID 58424758, compound

HRID 1408816Notes

Reaction equation

HRID 1408816 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:11]3([CH2:16][CH2:15][S:14][C:13]([NH:17]C(=O)OC(C)(C)C)=[N:12]3)[CH2:10][CH:9]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:8][C:5]2=[CH:6][CH:7]=1.[C:31]([C:33]1C=C(B(O)O)[CH:36]=[CH:37][CH:38]=1)#[N:32].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:25]1([CH:9]2[CH2:10][C:11]3([CH2:16][CH2:15][S:14][C:13]([NH2:17])=[N:12]3)[C:4]3[C:5](=[CH:6][CH:7]=[C:2]([C:37]4[CH:36]=[N:32][CH:31]=[CH:33][CH:38]=4)[CH:3]=3)[O:8]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27343253-Cyanophenylboronic acidHCID 58424577HCID 58424577, compound

Product 1

HCID 58424758HCID 58424758, compoundYield 5.5%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of t-butyl 6-bromo-2-phenyl-5′,6′-dihydrospiro[chroman-4,4′-[1,3]thiazine]-2′-ylcarbamate (39 mg, 0.08 mmol), 3-cyanophenylboronic acid (19.7 mg, 0.16 mmol), and Cs2CO3 (120 mg) in 1,4-dioxane (4 mL) and H2O (0.5 mL) charged in a 10 mL CEM microwave test tube is added PdCl2(PPh3)2 (20 mg). The system is degassed by sweeping with N2. The tube is capped and heated to 110° C. for 30 min in a CEM microwave reactor. Solvent is removed in vacuo and the residue is purified by preparative HPLC to give 2-phenyl-6-(pyridin-3-yl)-5′,6′-dihydrospiro[chroman-4,4′-[1,3]thiazin]-2′-amine (1.7 mg) as a TFA salt. MS ESI+ve m/z 389 (M+H)+.

Workup

  1. customThe system is degassed
  2. customThe tube is capped
  3. customSolvent is removed in vacuo
  4. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-9a18f1650dc94427802490c72e9963aa
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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