Hydrochloric Acid → HCID 58423756, compound

HRID 2096626Notes

Reaction equation

HRID 2096626 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)OC2=[CH:6][CH:7]=1.[C:31]([C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1)#[N:32].[C:42]([O-:45])([O-])=O.[Cs+].[Cs+].Cl>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:17][C:13]1[S:14][CH2:15][CH2:16][C:11]2([C:4]3[C:42](=[CH:6][CH:7]=[C:2]([C:35]4[CH:34]=[C:33]([CH:38]=[CH:37][CH:36]=4)[C:31]#[N:32])[CH:3]=3)[O:45][CH:9]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:10]2)[N:12]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 27343253-Cyanophenylboronic acidHCID 58424577HCID 58424577, compound

Product 1

HCID 58423756HCID 58423756, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of t-butyl 6-bromo-2-phenyl-5′,6′-dihydrospiro[chroman-4,4′-[1,3]thiazine]-2′-ylcarbamate (41 mg, 0.084 mmol), 3-cyanophenylboronic acid (23.5 mg, 0.16 mmol), Cs2CO3 (78 mg, 0.24 mmol), and a catalytic amount of Pd(dppf)Cl2 in 1,4-dioxane (4 mL) and H2O (0.4 mL) is heated at 110° C. in microwave oven for 10 min. Then, 4 mL of 4 M HCl in 1,4-dioxane is added and stirred another 2 h at rt. Water (10 mL) is added and extracted with EA. The separated organic phase is washed with brine, and dried over Na2SO4, and filtered. The filtrate is concentrated to give a crude product which is purified through preparative HPLC to give 3-(2′-amino-2-phenyl-5′,6′-dihydrospiro[chroman-4,4′-[1,3]thiazine]-6-yl)benzonitrile. MS ESI +ve m/z 412 (M+H)+.

Workup

  1. extractionextracted with EA
  2. washThe separated organic phase is washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated
  6. customto give a crude product which
  7. customis purified through preparative HPLC

Sources & evidence

ORD record
ord-10b9e432259944e4a4650da0165d85f8
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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