Water → 6,6-dimethyl-2-(6-(6-methylpyridin-3-yl)-2,3-dihydrobenzo[b][1,4]oxazin-4-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one

HRID 885961Notes

Reaction equation

HRID 885961 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([C:11]3[S:12][C:13]4[CH2:14]C(C)(C)N[C:17](=O)[C:18]=4[N:19]=3)[C:6]=2[CH:23]=1.[CH3:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][N:26]=1.C([O-])([O-])=O.[Na+].[Na+].[OH2:40]>C1COCC1>[CH3:5][C:6]1([CH3:23])[NH:7][C:14](=[O:40])[C:13]2[S:12][C:11]([N:7]3[C:6]4[CH:23]=[C:2]([C:28]5[CH:27]=[N:26][C:25]([CH3:24])=[CH:30][CH:29]=5)[CH:3]=[CH:4][C:5]=4[O:10][CH2:9][CH2:8]3)=[N:19][C:18]=2[CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27630812-Methylpyridine-5-boronic acidHCID 685972362-(6-Bromo-2,3-dihydrobenzo[1,4]oxazin-4-yl)-6,6-dimethyl-6,7-dihydro-[1,3]thiazolo[5,4-d]pyridin-4(5h)-one

Product 1

HCID 445776396,6-dimethyl-2-(6-(6-methylpyridin-3-yl)-2,3-dihydrobenzo[b][1,4]oxazin-4-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-oneYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of Example 39 (0.090 g, 0.23 mmol), 2-methylpyridine-5-boronic acid (0.094 g, 0.69 mmol), Na2CO3 (0.073 g, 0.69 mmol) and tetrakis-(triphenylphosphine)palladium(0) (0.026 g, 0.02 mmol) in THF (3 mL) was heated to 160° C. under microwave irradiation for 30 minutes. After cooling to r.t., water (10 mL) was added and the resulting precipitate filtered off, washed with water (3×20 mL) and dried in vacuo. The solid was then triturated with EtOAc (3×20 mL) and DCM (2×20 mL), then concentrated in vacuo to give the title compound (0.027 g, 29%) as an off-white solid. δH (CDCl3) 8.71 (1H, d, J 2.3 Hz), 8.22 (1H, d, J 2.1 Hz), 7.75 (1H, dd, J 8.1 and J 2.4 Hz), 7.29 (1H, dd, J 7.9 and J 2.3 Hz), 7.22 (1H, d, J 7.9 Hz), 7.05 (1H, d, J 8.5 Hz), 5.30 (1H, br. s), 4.43-4.37 (2H, m), 4.22-4.16 (2H, m), 2.89 (2H, s), 2.60 (3H, s), 1.40 (6H, s). LCMS (ES+) 407.0 (M+H)+, RT 1.99 minutes (Method 1).

Workup

  1. filtrationthe resulting precipitate filtered off
  2. washwashed with water (3×20 mL)
  3. customdried in vacuo
  4. customThe solid was then triturated with EtOAc (3×20 mL) and DCM (2×20 mL)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c801913ff8ef4070806ca51088935325
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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