Potassium Phosphate, Tribasic → HCID 67188006, compound

HRID 885977Notes

Reaction equation

HRID 885977 reaction equation
[CH3:1][C:2]1([CH3:31])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[C:19](B5OC(C)(C)C(C)(C)O5)[CH:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1.Br[C:33]1[S:34][C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[CH:37]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:34]1[C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[CH:37]=[C:33]1[C:19]1[CH:20]=[CH:21][C:16]2[O:15][CH2:14][CH2:13][N:12]([C:10]3[S:9][C:5]4[C:6](=[O:8])[NH:7][C:2]([CH3:1])([CH3:31])[CH2:3][C:4]=4[N:11]=3)[C:17]=2[CH:18]=1

Participants

9

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 947862-Bromobenzo(b)thiopheneHCID 584916876,6-dimethyl-2-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one

Product 1

HCID 67188006HCID 67188006, compoundYield 7%

Reagents, catalysts & solvents 5

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of Example 292 (0.048 g, 0.109 mmol), 2-bromobenzothiophene (0.035 g, 0.163 mmol), potassium phosphate (0.045 g, 0.212 mmol), tetra-n-butyl-ammonium bromide (0.045 g, 0.140 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.008 g, 0.007 mmol) in THF (2 mL) and H2O (0.5 mL) was heated to 100° C. in a sealed vessel under a nitrogen atmosphere for 1 h. The reaction mixture was diluted with DCM (10 mL) and washed with water (10 mL) and brine (10 mL). The organic fraction was dried (MgSO4) and concentrated in vacuo. Purification by preparative HPLC (Method 6) gave the title compound (0.003 g, 7%) as a white solid. δH (CDCl3) 8.35 (1H, d, J 2.1 Hz), 7.88-7.73 (2H, m), 7.46 (1H, s), 7.41 (1H, dd, J 8.5 and 2.1 Hz), 7.37-7.28 (2H, m), 7.01 (1H, d, J 8.5 Hz), 5.27 (1H, s), 4.42-4.35 (2H, m), 4.23-4.17 (2H, m), 2.91 (2H, s), 1.42 (6H, s). LCMS (ES+) 448 (M+H)+, RT 4.37 minutes (Method 1).

Workup

  1. washwashed with water (10 mL) and brine (10 mL)
  2. dry with materialThe organic fraction was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by preparative HPLC (Method 6)

Sources & evidence

ORD record
ord-2ee45f7cf75647b990a03ba54dab1e8b
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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